2-(dimethylamino)ethyl acetate

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

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

Procedure: With gentle cooling, 168.5 g of acetic anhydride are added dropwise to 133.6 g of 2-dimethylaminoethanol in the course of 20 minutes, whereupon the temperature rises from 20° C. to a maximum of 105° C. The reaction mixture is kept for 30 minutes at 100° C. and then cooled. Then 750 ml of CHCl3 are added and the acetic acid formed is neutralised with 380 ml of 20% sodium hydroxide solution at 30°-35° C. with cooling. The two phases are separated and the organic phase is washed with a small amount of H2O. Distillation of the residue affords 151.7 g (77.7%) of product with a boiling point of 114° C./225 torr. rises from 20° C. to a maximum of 105° C cooled with cooling The two phases are separated the organic phase is washed with a small amount of H2O Distillation of the residue

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

Procedure: With gentle cooling, 168.5 g of acetic anhydride are added dropwise to 133.6 g of 2-dimethylaminoethanol in the course of 20 minutes, whereupon the temperature rises from 20° C. to a maximum of 105° C. The reaction mixture is kept for 30 minutes at 100° C. and then cooled. Then 750 ml of CHCl3 are added and the acetic acid formed is neutralised with 380 ml of 20% sodium hydroxide solution at 30°-35° C. with cooling. The two phases are separated and the organic phase is washed with a small amount of H2O. Distillation of the residue affords 151.7 g (77.7%) of product with a boiling point of 114° C./225 torr. rises from 20° C. to a maximum of 105° C cooled with cooling The two phases are separated the organic phase is washed with a small amount of H2O Distillation of the residue

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

Conditions: temp:18.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a two-necked, round bottomed flask, equipped with a condenser and addition funnel, the 2-(dimethylamino)ethyl acetate (0.05 mol) was mixed with 30 mL of anhydrous hexane. Chloromethyl dodecyl ether (0.055 mol) was slowly added over 5 minutes. After 15 minutes, the reaction mixture was cooled to the temperature of minus 18° C. and the crude product was separated. The precipitate was washed with 30 mL of hexane and used in the next step without further purification. The crude (2-acetooxyethyl)-dodecyloxymethyldimethylammonium chloride was dissolved in 30 mL of water and aqueous solution of potassium benzoate (0.065 mol) was added. After 30 min, 30 mL of chloroform was added. The chloroform phase was separated and washed with distilled water until chloride ions were no longer detected using AgNO3. The obtained grease was dried under vacuum. The product was obtained as grease in 67% yield. Thermogravimetric analysis: Tonset=122° C. 1H and 13C NMR (DMSO) were obtained. In a two-necked, round bottomed flask, equipped with a condenser and addition funnel the crude product was separated The precipitate was washed with 30 mL of hexane used in the next step without further purification The crude (2-acetooxyethyl)-dodecyloxymethyldimethylammonium chloride was dissolved in 30 mL of water After 30 min The chloroform phase was separated washed with distilled water until chloride ions The obtained grease was dried under vacuum The product was obtained as grease in 67% yield Tonset=122° C

Conditions: temp:18.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a two-necked, round bottomed flask, equipped with a condenser and addition funnel, 2-(dimethylamino)ethyl acetate (0.1 mol) was mixed with 150 mL of anhydrous hexane. Chloromethyl hexyl ether (0.1 mol) was slowly added over 15 minutes. After 30 minutes, the reaction mixture was cooled to the temperature of minus 18° C. and the crude product was separated. The crude product was washed with 100 mL of hexane and used in the next step without further purification. The material was dissolved in 100 mL of water and aqueous solution of sodium benzoate was added in stoichiometric amount. After 30 minutes, two phases were separated. The water phase was removed and 100 mL of anhydrous acetone was added to the residue. Precipitated NaCl was filtered off and the obtained liquid product, (2-acetoxyethyl)heptyloxymethyldimethylammonium benzoate, was dried for 12 h at 60° C. in vacuum. The product was obtained as viscous liquid in 65% yield. Thermogravimetric analysis: Tonset=120° C. 1H and 13C NMR (DMSO) were obtained. In a two-necked, round bottomed flask, equipped with a condenser and addition funnel the crude product was separated The crude product was washed with 100 mL of hexane used in the next step without further purification The material was dissolved in 100 mL of water aqueous solution of sodium benzoate was added in stoichiometric amount After 30 minutes two phases were separated The water phase was removed 100 mL of anhydrous acetone was added to the residue Precipitated NaCl was filtered off the obtained liquid product, (2-acetoxyethyl)heptyloxymethyldimethylammonium benzoate, was dried for 12 h at 60° C. in vacuum The product was obtained as viscous liquid in 65% yield Tonset=120° C

Conditions: temp:18.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a two-necked, round bottomed flask, equipped with a condenser and addition funnel, 2-(dimethylamino)ethyl acetate (0.1 mol) was mixed with 150 mL of anhydrous hexane. Chloromethyl hexyl ether (0.1 mol) was slowly added over 15 minutes. After 30 minutes, the reaction mixture was cooled to the temperature of minus 18° C. and the crude product was separated. The crude product was washed with 100 mL of hexane and used in the next step without further purification. The material was dissolved in 100 mL of water and aqueous solution of sodium benzoate was added in stoichiometric amount. After 30 minutes, two phases were separated. The water phase was removed and 100 mL of anhydrous acetone was added to the residue. Precipitated NaCl was filtered off and the obtained liquid product, (2-acetoxyethyl)heptyloxymethyldimethylammonium benzoate, was dried for 12 h at 60° C. in vacuum. The product was obtained as viscous liquid in 65% yield. Thermogravimetric analysis: Tonset=120° C. 1H and 13C NMR (DMSO) were obtained. In a two-necked, round bottomed flask, equipped with a condenser and addition funnel the crude product was separated The crude product was washed with 100 mL of hexane used in the next step without further purification The material was dissolved in 100 mL of water aqueous solution of sodium benzoate was added in stoichiometric amount After 30 minutes two phases were separated The water phase was removed 100 mL of anhydrous acetone was added to the residue Precipitated NaCl was filtered off the obtained liquid product, (2-acetoxyethyl)heptyloxymethyldimethylammonium benzoate, was dried for 12 h at 60° C. in vacuum The product was obtained as viscous liquid in 65% yield Tonset=120° C

Conditions: temp:18.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a two-necked, round bottomed flask, equipped with a condenser and addition funnel, 2-(dimethylamino)ethyl acetate (0.1 mol) was mixed with 150 mL of anhydrous hexane. Chloromethyl hexyl ether (0.1 mol) was slowly added over 15 minutes. After 30 minutes, the reaction mixture was cooled to the temperature of minus 18° C. and the crude product was separated. The crude product was washed with 100 mL of hexane and used in the next step without further purification. The material was dissolved in 100 mL of water and aqueous solution of sodium benzoate was added in stoichiometric amount. After 30 minutes, two phases were separated. The water phase was removed and 100 mL of anhydrous acetone was added to the residue. Precipitated NaCl was filtered off and the obtained liquid product, (2-acetoxyethyl)heptyloxymethyldimethylammonium benzoate, was dried for 12 h at 60° C. in vacuum. The product was obtained as viscous liquid in 65% yield. Thermogravimetric analysis: Tonset=120° C. 1H and 13C NMR (DMSO) were obtained. In a two-necked, round bottomed flask, equipped with a condenser and addition funnel the crude product was separated The crude product was washed with 100 mL of hexane used in the next step without further purification The material was dissolved in 100 mL of water aqueous solution of sodium benzoate was added in stoichiometric amount After 30 minutes two phases were separated The water phase was removed 100 mL of anhydrous acetone was added to the residue Precipitated NaCl was filtered off the obtained liquid product, (2-acetoxyethyl)heptyloxymethyldimethylammonium benzoate, was dried for 12 h at 60° C. in vacuum The product was obtained as viscous liquid in 65% yield Tonset=120° C

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

Procedure: With gentle cooling, 168.5 g of acetic anhydride are added dropwise to 133.6 g of 2-dimethylaminoethanol in the course of 20 minutes, whereupon the temperature rises from 20° C. to a maximum of 105° C. The reaction mixture is kept for 30 minutes at 100° C. and then cooled. Then 750 ml of CHCl3 are added and the acetic acid formed is neutralised with 380 ml of 20% sodium hydroxide solution at 30°-35° C. with cooling. The two phases are separated and the organic phase is washed with a small amount of H2O. Distillation of the residue affords 151.7 g (77.7%) of product with a boiling point of 114° C./225 torr. rises from 20° C. to a maximum of 105° C cooled with cooling The two phases are separated the organic phase is washed with a small amount of H2O Distillation of the residue

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

Procedure: With gentle cooling, 168.5 g of acetic anhydride are added dropwise to 133.6 g of 2-dimethylaminoethanol in the course of 20 minutes, whereupon the temperature rises from 20° C. to a maximum of 105° C. The reaction mixture is kept for 30 minutes at 100° C. and then cooled. Then 750 ml of CHCl3 are added and the acetic acid formed is neutralised with 380 ml of 20% sodium hydroxide solution at 30°-35° C. with cooling. The two phases are separated and the organic phase is washed with a small amount of H2O. Distillation of the residue affords 151.7 g (77.7%) of product with a boiling point of 114° C./225 torr. rises from 20° C. to a maximum of 105° C cooled with cooling The two phases are separated the organic phase is washed with a small amount of H2O Distillation of the residue

Conditions: temp:18.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a two-necked, round bottomed flask, equipped with a condenser and addition funnel, the 2-(dimethylamino)ethyl acetate (0.05 mol) was mixed with 30 mL of anhydrous hexane. Chloromethyl dodecyl ether (0.055 mol) was slowly added over 5 minutes. After 15 minutes, the reaction mixture was cooled to the temperature of minus 18° C. and the crude product was separated. The precipitate was washed with 30 mL of hexane and used in the next step without further purification. The crude (2-acetooxyethyl)-dodecyloxymethyldimethylammonium chloride was dissolved in 30 mL of water and aqueous solution of potassium benzoate (0.065 mol) was added. After 30 min, 30 mL of chloroform was added. The chloroform phase was separated and washed with distilled water until chloride ions were no longer detected using AgNO3. The obtained grease was dried under vacuum. The product was obtained as grease in 67% yield. Thermogravimetric analysis: Tonset=122° C. 1H and 13C NMR (DMSO) were obtained. In a two-necked, round bottomed flask, equipped with a condenser and addition funnel the crude product was separated The precipitate was washed with 30 mL of hexane used in the next step without further purification The crude (2-acetooxyethyl)-dodecyloxymethyldimethylammonium chloride was dissolved in 30 mL of water After 30 min The chloroform phase was separated washed with distilled water until chloride ions The obtained grease was dried under vacuum The product was obtained as grease in 67% yield Tonset=122° C

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

Procedure: With gentle cooling, 168.5 g of acetic anhydride are added dropwise to 133.6 g of 2-dimethylaminoethanol in the course of 20 minutes, whereupon the temperature rises from 20° C. to a maximum of 105° C. The reaction mixture is kept for 30 minutes at 100° C. and then cooled. Then 750 ml of CHCl3 are added and the acetic acid formed is neutralised with 380 ml of 20% sodium hydroxide solution at 30°-35° C. with cooling. The two phases are separated and the organic phase is washed with a small amount of H2O. Distillation of the residue affords 151.7 g (77.7%) of product with a boiling point of 114° C./225 torr. rises from 20° C. to a maximum of 105° C cooled with cooling The two phases are separated the organic phase is washed with a small amount of H2O Distillation of the residue