4-dodecylaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A 2.3-g portion (0.005 mole) of 2,4,6-triphenylpyrylium triflate is placed in a 500-ml round-bottom flask. To this, 200 ml of ethanol is added and then 1.3 g (0.005 mole) of p-dodecylaniline is added. The mixture is refluxed for about 20 hours. The ethanol is removed by evaporation to give a yellow waxy substance. This material is washed with ether which causes some yellow crystals to precipitate. The mixture is refluxed for about 20 hours The ethanol is removed by evaporation to give a yellow waxy substance This material is washed with ether which to precipitate

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

Procedure: 4-Dodecylaniline (15.7 g) was dissolved in 100 mL of benzene and then 2-ethoxycarbonylcyclohexane (10.2 g) was added, followed by 0.20 g of p-toluenesulfonic acid. The reaction mixture was stirred for three days and then refluxed for 2 hours with the separation of H2O. The benzene was evaporated from this mixture, which was then dissolved in 100 mL of phenyl ether and refluxed for 45 minutes. At the end of this time the reaction mixture was allowed to cool and the precipitated product was filtered off. This crude product was purified by flash chromatography (20% ethyl acetate/CH2Cl2) and then recrystallized from 1,2-dichloroethane/methanol to give 1.31 g, mp 225°-226°. The benzene was evaporated from this mixture, which was then dissolved in 100 mL of phenyl ether refluxed for 45 minutes to cool the precipitated product was filtered off This crude product was purified by flash chromatography (20% ethyl acetate/CH2Cl2) recrystallized from 1,2-dichloroethane/methanol to give 1.31 g, mp 225°-226°

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

Procedure: 4-Dodecylaniline (15.7 g) was dissolved in 100 mL of benzene and then 2-ethoxycarbonylcyclohexane (10.2 g) was added, followed by 0.20 g of p-toluenesulfonic acid. The reaction mixture was stirred for three days and then refluxed for 2 hours with the separation of H2O. The benzene was evaporated from this mixture, which was then dissolved in 100 mL of phenyl ether and refluxed for 45 minutes. At the end of this time the reaction mixture was allowed to cool and the precipitated product was filtered off. This crude product was purified by flash chromatography (20% ethyl acetate/CH2Cl2) and then recrystallized from 1,2-dichloroethane/methanol to give 1.31 g, mp 225°-226°. The benzene was evaporated from this mixture, which was then dissolved in 100 mL of phenyl ether refluxed for 45 minutes to cool the precipitated product was filtered off This crude product was purified by flash chromatography (20% ethyl acetate/CH2Cl2) recrystallized from 1,2-dichloroethane/methanol to give 1.31 g, mp 225°-226°

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1-liter flask fitted with a stirrer and reflux condenser is added 137.5 grams (0.525 mole) of p-n-dodecylaniline, dissolved in 138 ml of toluene. To this is added over a 15-minute period 57.5 ml of acetic anhydride. The temperature rises from 40° to 80° C. After all the acetic anhydride is added, the reaction mixture is stirred at 40° C. for 3 hours. The reaction mixture is then cooled to yield the crude product which is recrystallized from 800 ml of methanol to give 151.1 grams of the above-named material as a solid melting at 100°-102° C. In a 1-liter flask fitted with a stirrer reflux condenser rises from 40° to 80° C The reaction mixture is then cooled to yield the crude product which is recrystallized from 800 ml of methanol

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

Procedure: solution of acetophenone (33.5 g), p-dodecyl aniline (73 g), benzene (50 ml) was refluxed in the presence of molecular sieve (100 g) with continuous removal of water. The crude product was purified by crystallizing it from ethanol to give N-(α-methyl benzylidene)-p-dodecyl aniline (V) (95 g). V had a melting point of 47° C. The crude product was purified by crystallizing it from ethanol

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: A 2.3-g portion (0.005 mole) of 2,4,6-triphenylpyrylium triflate is placed in a 500-ml round-bottom flask. To this, 200 ml of ethanol is added and then 1.3 g (0.005 mole) of p-dodecylaniline is added. The mixture is refluxed for about 20 hours. The ethanol is removed by evaporation to give a yellow waxy substance. This material is washed with ether which causes some yellow crystals to precipitate. The mixture is refluxed for about 20 hours The ethanol is removed by evaporation to give a yellow waxy substance This material is washed with ether which to precipitate

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

Procedure: A 2.3-g portion (0.005 mole) of 2,4,6-triphenylpyrylium triflate is placed in a 500-ml round-bottom flask. To this, 200 ml of ethanol is added and then 1.3 g (0.005 mole) of p-dodecylaniline is added. The mixture is refluxed for about 20 hours. The ethanol is removed by evaporation to give a yellow waxy substance. This material is washed with ether which causes some yellow crystals to precipitate. The mixture is refluxed for about 20 hours The ethanol is removed by evaporation to give a yellow waxy substance This material is washed with ether which to precipitate

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