2-[2-(azocan-1-yl)ethyl]guanidine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: First, 12 g (0.046 mol) of paradodecyl aniline was dissolved in 100 mL of THF and then put into a 100 mL three-neck round bottom flask. To this solution was added dropwise through a funnel over 10 minutes an acid remover prepared by mixing imidazole and triethyl amine at an equivalent mole ratio (0.023 mol). Then, to the resulting solution was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared by dissolving 3.8 ml (0.047 mol) of acryloyl chloride in 20 mL of THF. At this time, the reaction mixture cooled with ice so as to keep its temperature below 5° C. Thereafter, the reaction proceeded at 0° C. for 6 hours, and then at 25° C. for 9 hours. After the completion of the reaction, the resulting solution was filtered with a filtering paper to remove salt precipitates, and then the solvent was eliminated by using an evaporator. The obtained solids were dissolved in 100 mL of dichloromethane and put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 and shaken strongly to separate the aqueous solution layer and to remove the unreacted portion of acryloyl chloride. To the dichloromethane solution being separated was added 1.0 g of magnesium sulfate and the resulting mixture was stirred for 5 hours and filtered to remove a trace amount of water being dissolved in the solvent. The resulting dichloromethane solution was evaporated and then 100 mL of n-hexane was added thereto and stirred for 2 hours, and then was filtered to remove the unreacted portion of paradodecyl aniline remained in the solution. The solvent was removed from the resulting solution by using an evaporator to provide white solids of DOPAM (Yield: 95%). The chemical structure of DOPAM as synthesized was confirmed by a 1H nuclear magnetic resonance (1H-NMR) spectrum, and the results are the same as follows: put into a 100 mL three-neck round bottom flask To this solution was added dropwise through a funnel over 10 minutes an acid remover prepared Then, to the resulting solution was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared At this time, the reaction mixture cooled with ice so as its temperature below 5° C at 25° C. for 9 hours After the completion of the reaction the resulting solution was filtered with a filtering paper to remove salt precipitates an evaporator The obtained solids were dissolved in 100 mL of dichloromethane put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 to separate the aqueous solution layer to remove the unreacted portion of acryloyl chloride To the dichloromethane solution being separated was added 1.0 g of magnesium sulfate the resulting mixture was stirred for 5 hours filtered to remove a trace amount of water being dissolved in the solvent The resulting dichloromethane solution was evaporated 100 mL of n-hexane was added stirred for 2 hours was filtered to remove the unreacted portion of paradodecyl aniline The solvent was removed from the resulting solution an evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: First, 12 g (0.046 mol) of paradodecyl aniline was dissolved in 100 mL of THF and then put into a 100 mL three-neck round bottom flask. To this solution was added dropwise through a funnel over 10 minutes an acid remover prepared by mixing imidazole and triethyl amine at an equivalent mole ratio (0.023 mol). Then, to the resulting solution was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared by dissolving 3.8 mL (0.047 mol) of acryloyl chloride in 20 mL of THF. At this time, the reaction mixture cooled with ice so as to keep its temperature below 5° C. Thereafter, the reaction proceeded at 0° C. for 6 hours, and then at 25° C. for 9 hours. After the completion of the reaction, the resulting solution was filtered with a filtering paper to remove salt precipitates, and then the solvent was eliminated by using an evaporator. The obtained solids were dissolved in 100 mL of dichloromethane and put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 and shaken strongly to separate the aqueous solution layer and to remove the unreacted portion of acryloyl chloride. To the dichloromethane solution being separated was added 1.0 g of magnesium sulfate and the resulting mixture was stirred for 5 hours and filtered to remove a trace amount of water being dissolved in the solvent. The resulting dichloromethane solution was evaporated and then 100 mL of n-hexane was added thereto and stirred for 2 hours, and then was filtered to remove an unreacted portion of paradodecyl aniline remained in the solution. The solvent was removed from the resulting solution by using an evaporator to provide white solids of DOPAM (Yield: 95%). The chemical structure of DOPAM as synthesized was confirmed by a 1H nuclear magnetic resonance (1H-NMR) spectrum, and the results are the same as follows: put into a 100 mL three-neck round bottom flask To this solution was added dropwise through a funnel over 10 minutes an acid remover prepared Then, to the resulting solution was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared At this time, the reaction mixture cooled with ice so as its temperature below 5° C at 25° C. for 9 hours After the completion of the reaction the resulting solution was filtered with a filtering paper to remove salt precipitates an evaporator The obtained solids were dissolved in 100 mL of dichloromethane put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 to separate the aqueous solution layer to remove the unreacted portion of acryloyl chloride To the dichloromethane solution being separated was added 1.0 g of magnesium sulfate the resulting mixture was stirred for 5 hours filtered to remove a trace amount of water being dissolved in the solvent The resulting dichloromethane solution was evaporated 100 mL of n-hexane was added stirred for 2 hours was filtered to remove an unreacted portion of paradodecyl aniline The solvent was removed from the resulting solution an evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Firstly, p-dodecylaniline (12 g, 0.046 mol) was dissolved in THF solvent (100 mL). The solution was poured into a 100 mL three-mouthed round flask, and an acid eliminator was added dropwise through a funnel for 10 minutes, where the acid eliminator contained imidazole and triethyl amine at the same mole fraction (0.023 mol). Under the nitrogen atmosphere, a solution containing acryloyl chloride (3.8 mL, 0.047 mol) in THF (20 mL) was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes. Meanwhile, the solution was cooled on ice bath to prevent the temperature of the reaction mixture from rising above 5° C. After 6 hours of reaction at 0° C., the solution was kept at 25° C. for more 9 hours of reaction. Upon completion of the reaction, the solution was passed through a filter paper to eliminate precipitated salts, and the solvent was evaporated from the filtrate on an evaporator. The solid thus obtained was dissolved in dichloromethane (100 mL) and added to a separatory funnel along with 10% aqueous NaHCO3 solution (50 mL). The funnel was shaken vigorously and set aside to allow for the complete separation of the aqueous phase and thereby to remove unreacted acryloyl chloride. Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution. After stirred for 5 hours, the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent. The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added. The solution was stirred for 2 hours, and unreacted p-dodecyl aniline was filtered out from the solution. The filtrate was then removed of the solvent on the evaporator to yield a white solid DOPAM product (yield 95%). The chemical structure of the DOPAM product was identified by hydrogen nuclear magnetic resonance (1H-NMR) spectrum. The results were as follows. an acid eliminator was added dropwise through a funnel for 10 minutes was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes Meanwhile, the solution was cooled on ice bath from rising above 5° C After 6 hours of reaction at 0° C. the solution was kept at 25° C. for more 9 hours of reaction Upon completion of the reaction to eliminate precipitated salts the solvent was evaporated from the filtrate on an evaporator The solid thus obtained to allow for the complete separation of the aqueous phase to remove unreacted acryloyl chloride Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution After stirred for 5 hours the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added The solution was stirred for 2 hours unreacted p-dodecyl aniline was filtered out from the solution The filtrate was then removed of the solvent on the evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Firstly, p-dodecylaniline (12 g, 0.046 mol) was dissolved in THF solvent (100 mL). The solution was poured into a 100 mL three-mouthed round flask, and an acid eliminator was added dropwise through a funnel for 10 minutes, where the acid eliminator contained imidazole and triethyl amine at the same mole fraction (0.023 mol). Under the nitrogen atmosphere, a solution containing acryloyl chloride (3.8 mL, 0.047 mol) in THF (20 mL) was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes. Meanwhile, the solution was cooled on ice bath to prevent the temperature of the reaction mixture from rising above 5° C. After 6 hours of reaction at 0° C., the solution was kept at 25° C. for more 9 hours of reaction. Upon completion of the reaction, the solution was passed through a filter paper to eliminate precipitated salts, and the solvent was evaporated from the filtrate on an evaporator. The solid thus obtained was dissolved in dichloromethane (100 mL) and added to a separatory funnel along with 10% aqueous NaHCO3 solution (50 mL). The funnel was shaken vigorously and set aside to allow for the complete separation of the aqueous phase and thereby to remove unreacted acryloyl chloride. Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution. After stirred for 5 hours, the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent. The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added. The solution was stirred for 2 hours, and unreacted p-dodecyl aniline was filtered out from the solution. The filtrate was then removed of the solvent on the evaporator to yield a white solid DOPAM product (yield 95%). The chemical structure of the DOPAM product was identified by hydrogen nuclear magnetic resonance (1H-NMR) spectrum. The results were as follows. an acid eliminator was added dropwise through a funnel for 10 minutes was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes Meanwhile, the solution was cooled on ice bath from rising above 5° C After 6 hours of reaction at 0° C. the solution was kept at 25° C. for more 9 hours of reaction Upon completion of the reaction to eliminate precipitated salts the solvent was evaporated from the filtrate on an evaporator The solid thus obtained to allow for the complete separation of the aqueous phase to remove unreacted acryloyl chloride Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution After stirred for 5 hours the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added The solution was stirred for 2 hours unreacted p-dodecyl aniline was filtered out from the solution The filtrate was then removed of the solvent on the evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Firstly, p-dodecylaniline (12 g, 0.046 mol) was dissolved in THF solvent (100 mL). The solution was poured into a 100 mL three-mouthed round flask, and an acid eliminator was added dropwise through a funnel for 10 minutes, where the acid eliminator contained imidazole and triethyl amine at the same mole fraction (0.023 mol). Under the nitrogen atmosphere, a solution containing acryloyl chloride (3.8 mL, 0.047 mol) in THF (20 mL) was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes. Meanwhile, the solution was cooled on ice bath to prevent the temperature of the reaction mixture from rising above 5° C. After 6 hours of reaction at 0° C., the solution was kept at 25° C. for more 9 hours of reaction. Upon completion of the reaction, the solution was passed through a filter paper to eliminate precipitated salts, and the solvent was evaporated from the filtrate on an evaporator. The solid thus obtained was dissolved in dichloromethane (100 mL) and added to a separatory funnel along with 10% aqueous NaHCO3 solution (50 mL). The funnel was shaken vigorously and set aside to allow for the complete separation of the aqueous phase and thereby to remove unreacted acryloyl chloride. Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution. After stirred for 5 hours, the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent. The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added. The solution was stirred for 2 hours, and unreacted p-dodecyl aniline was filtered out from the solution. The filtrate was then removed of the solvent on the evaporator to yield a white solid DOPAM product (yield 95%). The chemical structure of the DOPAM product was identified by hydrogen nuclear magnetic resonance (1H-NMR) spectrum. The results were as follows. an acid eliminator was added dropwise through a funnel for 10 minutes was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes Meanwhile, the solution was cooled on ice bath from rising above 5° C After 6 hours of reaction at 0° C. the solution was kept at 25° C. for more 9 hours of reaction Upon completion of the reaction to eliminate precipitated salts the solvent was evaporated from the filtrate on an evaporator The solid thus obtained to allow for the complete separation of the aqueous phase to remove unreacted acryloyl chloride Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution After stirred for 5 hours the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added The solution was stirred for 2 hours unreacted p-dodecyl aniline was filtered out from the solution The filtrate was then removed of the solvent on the evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Firstly, p-dodecylaniline (12 g, 0.046 mol) was dissolved in THF solvent (100 mL). The solution was poured into a 100 mL three-mouthed round flask, and an acid eliminator was added dropwise through a funnel for 10 minutes, where the acid eliminator contained imidazole and triethyl amine at the same mole fraction (0.023 mol). Under the nitrogen atmosphere, a solution containing acryloyl chloride (3.8 mL, 0.047 mol) in THF (20 mL) was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes. Meanwhile, the solution was cooled on ice bath to prevent the temperature of the reaction mixture from rising above 5° C. After 6 hours of reaction at 0° C., the solution was kept at 25° C. for more 9 hours of reaction. Upon completion of the reaction, the solution was passed through a filter paper to eliminate precipitated salts, and the solvent was evaporated from the filtrate on an evaporator. The solid thus obtained was dissolved in dichloromethane (100 mL) and added to a separatory funnel along with 10% aqueous NaHCO3 solution (50 mL). The funnel was shaken vigorously and set aside to allow for the complete separation of the aqueous phase and thereby to remove unreacted acryloyl chloride. Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution. After stirred for 5 hours, the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent. The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added. The solution was stirred for 2 hours, and unreacted p-dodecyl aniline was filtered out from the solution. The filtrate was then removed of the solvent on the evaporator to yield a white solid DOPAM product (yield 95%). The chemical structure of the DOPAM product was identified by hydrogen nuclear magnetic resonance (1H-NMR) spectrum. The results were as follows. an acid eliminator was added dropwise through a funnel for 10 minutes was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes Meanwhile, the solution was cooled on ice bath from rising above 5° C After 6 hours of reaction at 0° C. the solution was kept at 25° C. for more 9 hours of reaction Upon completion of the reaction to eliminate precipitated salts the solvent was evaporated from the filtrate on an evaporator The solid thus obtained to allow for the complete separation of the aqueous phase to remove unreacted acryloyl chloride Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution After stirred for 5 hours the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added The solution was stirred for 2 hours unreacted p-dodecyl aniline was filtered out from the solution The filtrate was then removed of the solvent on the evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Firstly, p-dodecylaniline (12 g, 0.046 mol) was dissolved in THF solvent (100 mL). The solution was poured into a 100 mL three-mouthed round flask, and an acid eliminator was added dropwise through a funnel for 10 minutes, where the acid eliminator contained imidazole and triethyl amine at the same mole fraction (0.023 mol). Under the nitrogen atmosphere, a solution containing acryloyl chloride (3.8 mL, 0.047 mol) in THF (20 mL) was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes. Meanwhile, the solution was cooled on ice bath to prevent the temperature of the reaction mixture from rising above 5° C. After 6 hours of reaction at 0° C., the solution was kept at 25° C. for more 9 hours of reaction. Upon completion of the reaction, the solution was passed through a filter paper to eliminate precipitated salts, and the solvent was evaporated from the filtrate on an evaporator. The solid thus obtained was dissolved in dichloromethane (100 mL) and added to a separatory funnel along with 10% aqueous NaHCO3 solution (50 mL). The funnel was shaken vigorously and set aside to allow for the complete separation of the aqueous phase and thereby to remove unreacted acryloyl chloride. Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution. After stirred for 5 hours, the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent. The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added. The solution was stirred for 2 hours, and unreacted p-dodecyl aniline was filtered out from the solution. The filtrate was then removed of the solvent on the evaporator to yield a white solid DOPAM product (yield 95%). The chemical structure of the DOPAM product was identified by hydrogen nuclear magnetic resonance (1H-NMR) spectrum. The results were as follows. an acid eliminator was added dropwise through a funnel for 10 minutes was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes Meanwhile, the solution was cooled on ice bath from rising above 5° C After 6 hours of reaction at 0° C. the solution was kept at 25° C. for more 9 hours of reaction Upon completion of the reaction to eliminate precipitated salts the solvent was evaporated from the filtrate on an evaporator The solid thus obtained to allow for the complete separation of the aqueous phase to remove unreacted acryloyl chloride Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution After stirred for 5 hours the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added The solution was stirred for 2 hours unreacted p-dodecyl aniline was filtered out from the solution The filtrate was then removed of the solvent on the evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Firstly, p-dodecylaniline (12 g, 0.046 mol) was dissolved in THF solvent (100 mL). The solution was poured into a 100 mL three-mouthed round flask, and an acid eliminator was added dropwise through a funnel for 10 minutes, where the acid eliminator contained imidazole and triethyl amine at the same mole fraction (0.023 mol). Under the nitrogen atmosphere, a solution containing acryloyl chloride (3.8 mL, 0.047 mol) in THF (20 mL) was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes. Meanwhile, the solution was cooled on ice bath to prevent the temperature of the reaction mixture from rising above 5° C. After 6 hours of reaction at 0° C., the solution was kept at 25° C. for more 9 hours of reaction. Upon completion of the reaction, the solution was passed through a filter paper to eliminate precipitated salts, and the solvent was evaporated from the filtrate on an evaporator. The solid thus obtained was dissolved in dichloromethane (100 mL) and added to a separatory funnel along with 10% aqueous NaHCO3 solution (50 mL). The funnel was shaken vigorously and set aside to allow for the complete separation of the aqueous phase and thereby to remove unreacted acryloyl chloride. Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution. After stirred for 5 hours, the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent. The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added. The solution was stirred for 2 hours, and unreacted p-dodecyl aniline was filtered out from the solution. The filtrate was then removed of the solvent on the evaporator to yield a white solid DOPAM product (yield 95%). The chemical structure of the DOPAM product was identified by hydrogen nuclear magnetic resonance (1H-NMR) spectrum. The results were as follows. an acid eliminator was added dropwise through a funnel for 10 minutes was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes Meanwhile, the solution was cooled on ice bath from rising above 5° C After 6 hours of reaction at 0° C. the solution was kept at 25° C. for more 9 hours of reaction Upon completion of the reaction to eliminate precipitated salts the solvent was evaporated from the filtrate on an evaporator The solid thus obtained to allow for the complete separation of the aqueous phase to remove unreacted acryloyl chloride Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution After stirred for 5 hours the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added The solution was stirred for 2 hours unreacted p-dodecyl aniline was filtered out from the solution The filtrate was then removed of the solvent on the evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: First, 12 g (0.046 mol) of paradodecyl aniline was dissolved in 100 mL of THF and then put into a 100 mL three-neck round bottom flask. To the resulting mixture was added dropwise through a funnel for 10 minutes an acid remover prepared by mixing imidazole and triethyl amine at the same mole ratio (0.023 mol). Then, to the resulting mixture was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared by dissolving 3.8 ml (0.047 mol) of acryloyl chloride in 20 mL of THF. At this time, the reaction mixture cooled with ice in order for its temperature to be maintained below 5° C. Thereafter, the reaction proceeded at 0° C. for 6 hours, and at 25° C. for 9 hours. After the completion of the reaction, the resulting mixture was filtered with a filtering paper to remove salt precipitates, and then the solvent was eliminated by using an evaporator. The obtained solid was dissolved in 100 mL of dichloromethane and put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 and shaken strongly to separate the aqueous solution layer and remove an unreacted acryloyl chloride. To the dichloromethane solution as separated was added 1.0 g of magnesium sulfate and the resulting mixture was stirred for 5 hours and filtered so as to remove a trace amount of water being dissolved in the solvent. The resulting dichloromethane solution was evaporated and then 100 mL of n-hexane was added thereto and stirred for 2 hours, and then is filtered to remove an unreacted paradodecyl aniline remained in the solution. The solvent was removed from the resulting solution by using an evaporator to provide a white solid of DOPAM (Yield: 95%). The chemical structure of DOPAM as synthesized was confirmed by a 1H nuclear magnetic resonance (1H-NMR) spectrum, and the results are the same as follows: put into a 100 mL three-neck round bottom flask To the resulting mixture was added dropwise through a funnel for 10 minutes an acid remover prepared Then, to the resulting mixture was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared At this time, the reaction mixture cooled with ice in order for its temperature to be maintained below 5° C at 25° C. for 9 hours After the completion of the reaction the resulting mixture was filtered with a filtering paper to remove salt precipitates an evaporator The obtained solid was dissolved in 100 mL of dichloromethane put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 to separate the aqueous solution layer remove an unreacted acryloyl chloride To the dichloromethane solution as separated was added 1.0 g of magnesium sulfate the resulting mixture was stirred for 5 hours filtered so as to remove a trace amount of water being dissolved in the solvent The resulting dichloromethane solution was evaporated 100 mL of n-hexane was added stirred for 2 hours is filtered to remove an unreacted paradodecyl aniline The solvent was removed from the resulting solution an evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Firstly, p-dodecylaniline (12 g, 0.046 mol) was dissolved in THF solvent (100 mL). The solution was poured into a 100 mL three-mouthed round flask, and an acid eliminator was added dropwise through a funnel for 10 minutes, where the acid eliminator contained imidazole and triethyl amine at the same mole fraction (0.023 mol). Under the nitrogen atmosphere, a solution containing acryloyl chloride (3.8 mL, 0.047 mol) in THF (20 mL) was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes. Meanwhile, the solution was cooled on ice bath to prevent the temperature of the reaction mixture from rising above 5° C. After 6 hours of reaction at 0° C., the solution was kept at 25° C. for more 9 hours of reaction. Upon completion of the reaction, the solution was passed through a filter paper to eliminate precipitated salts, and the solvent was evaporated from the filtrate on an evaporator. The solid thus obtained was dissolved in dichloromethane (100 mL) and added to a separatory funnel along with 10% aqueous NaHCO3 solution (50 mL). The funnel was shaken vigorously and set aside to allow for the complete separation of the aqueous phase and thereby to remove unreacted acryloyl chloride. Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution. After stirred for 5 hours, the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent. The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added. The solution was stirred for 2 hours, and unreacted p-dodecyl aniline was filtered out from the solution. The filtrate was then removed of the solvent on the evaporator to yield a white solid DOPAM product (yield 95%). The chemical structure of the DOPAM product was identified by hydrogen nuclear magnetic resonance (1H-NMR) spectrum. The results were as follows. an acid eliminator was added dropwise through a funnel for 10 minutes was gradually added dropwise to the mixed solution through a dropping funnel for 20 minutes Meanwhile, the solution was cooled on ice bath from rising above 5° C After 6 hours of reaction at 0° C. the solution was kept at 25° C. for more 9 hours of reaction Upon completion of the reaction to eliminate precipitated salts the solvent was evaporated from the filtrate on an evaporator The solid thus obtained to allow for the complete separation of the aqueous phase to remove unreacted acryloyl chloride Magnesium sulfate (1.0 g) was added to the separated dichloromethane solution After stirred for 5 hours the solution was subjected to filtration to remove a trace amount of water dissolved in the solvent The dichloromethane solution thus obtained was kept on the evaporator, and n-hexane (100 mL) was added The solution was stirred for 2 hours unreacted p-dodecyl aniline was filtered out from the solution The filtrate was then removed of the solvent on the evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: First, 12 g (0.046 mol) of paradodecyl aniline was dissolved in 100 mL of THF and then put into a 100 mL three-neck round bottom flask. To this solution was added dropwise through a funnel over 10 minutes an acid remover prepared by mixing imidazole and triethyl amine at an equivalent mole ratio (0.023 mol). Then, to the resulting solution was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared by dissolving 3.8 ml (0.047 mol) of acryloyl chloride in 20 mL of THF. At this time, the reaction mixture cooled with ice so as to keep its temperature below 5° C. Thereafter, the reaction proceeded at 0° C. for 6 hours, and then at 25° C. for 9 hours. After the completion of the reaction, the resulting solution was filtered with a filtering paper to remove salt precipitates, and then the solvent was eliminated by using an evaporator. The obtained solids were dissolved in 100 mL of dichloromethane and put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 and shaken strongly to separate the aqueous solution layer and to remove the unreacted portion of acryloyl chloride. To the dichloromethane solution being separated was added 1.0 g of magnesium sulfate and the resulting mixture was stirred for 5 hours and filtered to remove a trace amount of water being dissolved in the solvent. The resulting dichloromethane solution was evaporated and then 100 mL of n-hexane was added thereto and stirred for 2 hours, and then was filtered to remove the unreacted portion of paradodecyl aniline remained in the solution. The solvent was removed from the resulting solution by using an evaporator to provide white solids of DOPAM (Yield: 95%). The chemical structure of DOPAM as synthesized was confirmed by a 1H nuclear magnetic resonance (1H-NMR) spectrum, and the results are the same as follows: put into a 100 mL three-neck round bottom flask To this solution was added dropwise through a funnel over 10 minutes an acid remover prepared Then, to the resulting solution was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared At this time, the reaction mixture cooled with ice so as its temperature below 5° C at 25° C. for 9 hours After the completion of the reaction the resulting solution was filtered with a filtering paper to remove salt precipitates an evaporator The obtained solids were dissolved in 100 mL of dichloromethane put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 to separate the aqueous solution layer to remove the unreacted portion of acryloyl chloride To the dichloromethane solution being separated was added 1.0 g of magnesium sulfate the resulting mixture was stirred for 5 hours filtered to remove a trace amount of water being dissolved in the solvent The resulting dichloromethane solution was evaporated 100 mL of n-hexane was added stirred for 2 hours was filtered to remove the unreacted portion of paradodecyl aniline The solvent was removed from the resulting solution an evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: First, 12 g (0.046 mol) of paradodecyl aniline was dissolved in 100 mL of THF and then put into a 100 mL three-neck round bottom flask. To this solution was added dropwise through a funnel over 10 minutes an acid remover prepared by mixing imidazole and triethyl amine at an equivalent mole ratio (0.023 mol). Then, to the resulting solution was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared by dissolving 3.8 mL (0.047 mol) of acryloyl chloride in 20 mL of THF. At this time, the reaction mixture cooled with ice so as to keep its temperature below 5° C. Thereafter, the reaction proceeded at 0° C. for 6 hours, and then at 25° C. for 9 hours. After the completion of the reaction, the resulting solution was filtered with a filtering paper to remove salt precipitates, and then the solvent was eliminated by using an evaporator. The obtained solids were dissolved in 100 mL of dichloromethane and put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 and shaken strongly to separate the aqueous solution layer and to remove the unreacted portion of acryloyl chloride. To the dichloromethane solution being separated was added 1.0 g of magnesium sulfate and the resulting mixture was stirred for 5 hours and filtered to remove a trace amount of water being dissolved in the solvent. The resulting dichloromethane solution was evaporated and then 100 mL of n-hexane was added thereto and stirred for 2 hours, and then was filtered to remove an unreacted portion of paradodecyl aniline remained in the solution. The solvent was removed from the resulting solution by using an evaporator to provide white solids of DOPAM (Yield: 95%). The chemical structure of DOPAM as synthesized was confirmed by a 1H nuclear magnetic resonance (1H-NMR) spectrum, and the results are the same as follows: put into a 100 mL three-neck round bottom flask To this solution was added dropwise through a funnel over 10 minutes an acid remover prepared Then, to the resulting solution was slowly added dropwise through a dropping funnel over 20 minutes under a nitrogen atmosphere a solution prepared At this time, the reaction mixture cooled with ice so as its temperature below 5° C at 25° C. for 9 hours After the completion of the reaction the resulting solution was filtered with a filtering paper to remove salt precipitates an evaporator The obtained solids were dissolved in 100 mL of dichloromethane put into a separating funnel together with 50 mL of an aqueous solution of 10% NaHCO3 to separate the aqueous solution layer to remove the unreacted portion of acryloyl chloride To the dichloromethane solution being separated was added 1.0 g of magnesium sulfate the resulting mixture was stirred for 5 hours filtered to remove a trace amount of water being dissolved in the solvent The resulting dichloromethane solution was evaporated 100 mL of n-hexane was added stirred for 2 hours was filtered to remove an unreacted portion of paradodecyl aniline The solvent was removed from the resulting solution an evaporator