dodecyl 2-(dimethylamino)acetate

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

Procedure: Dodecyl chloroacetate (5.5 g, 0.021 mol) was dissolved in 20 ml of ether and the resultant solution was cooled in an ice-bath. Dimethylamine (40 ml, 0.1M in ether) was added to the cooled solution of dodecyl chloroacetate. The reaction mixture was stirred at room temperature for two hours, then filtered through a filter paper to remove the white solid which formed. The filtrate was concentrated to give a liquid product which was chromatographed through a column of silica gel (60-200 mesh) using ethyl acetate as the eluent. The purity of the fractions was checked by thin layer chromatography. The pure fractions were combined and the solvent was removed by a rotary evaporator under reduced pressure to afford 5.8 g (100% yield) of dodecyl (N,N-dimethylamino)acetate. 1HNMR(CCl4) δ0.83(3H, t, CH3); 1.20[20 H, s, broad, --(CH2)10 ]; 2.23[6H, s, (CH3)2N--]; 3.0 (2H, s, --CH2 --N); 3.93 (2H, t, J=6 Hz, --OCH2 --). νmax (film): 2940, 2870, 2790 (CH); 1760, 1740(C=O); 1200, 1170 (--C--O --C) cm-1. m/e 271; C16H33NO2 requires 271. filtered through a filter paper to remove the white solid which formed The filtrate was concentrated to give a liquid product which was chromatographed through a column of silica gel (60-200 mesh) the solvent was removed by a rotary evaporator under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: First, 1-dodecyl alcohol (2.98 g, 0.016 mol), triethylamine (1.62 g, 0.016 mol) and 4-(N,N-dimethylamino)pyridine (DMAP; 0.195 g, 0.0016 mol) were added to a solution of N,N-dimethylglycine hydrochloride (2.23 g, 0.016 mol) in dry N,N-dimethylformamide (DMF; 100 mL) under nitrogen atmosphere, and cooled to 0° C. Then, dicyclohexylcarbodiimide (DCC; 3.63 g, 0.0176 mol) in dry DMF (60 ml) was added thereto at 0° C. The reaction mixture was returned to room temperature and stirred for about one day, then DMF was evaporated under reduced pressure with a pump. The residue was dissolved using ether and aqueous saturated sodium bicarbonate solution, and the ether layer was collected and washed once with water and once with saturated saline, after which it was dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The resultant residue was separated by column chromatography (hexane:ethyl acetate:triethylamine=50:50:1) to give N,N-dimethylamino-acetate-1-dodecyl ester (C12-tertiary amine) (yield 48%, 2.10 g). at 0° C was returned to room temperature DMF was evaporated under reduced pressure with a pump The residue was dissolved the ether layer was collected washed once with water and once with saturated saline after which it was dried over anhydrous magnesium sulfate the solvent was removed under reduced pressure The resultant residue was separated by column chromatography (hexane:ethyl acetate:triethylamine=50:50:1)

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

Procedure: Dodecyl chloroacetate (5.5 g, 0.021 mol) was dissolved in 20 ml of ether and the resultant solution was cooled in an ice-bath. Dimethylamine (40 ml, 0.1 M in ether) was added to the cooled solution of dodecyl chloroacetate. The reaction mixture was stirred at room temperature for two hours, then filtered through a filter paper to remove the white solid which formed. The filtrate was concentrated to give a liquid product which was chromatographed through a column of silica gel (60-200 mesh) using ethyl acetate as the eluent. The purity of the fractions was checked by thin layer chromatography. The pure fractions were combined and the solvent was removed by a rotary evaporator under reduced pressure to afford 5.8 g (100% yield) of dodecyl (N,N-dimethylamino)acetate. 1HNMR(CCl4) δ0.83(3H, t, CH3); 1.20[20 H, s, broad, --(CH2)10 ]; 2.23[6H, s, (CH3)2N--]; 3.0 (2H, s, --CH2 --N); 3.93 (2H, t, J=6 Hz, --OCH2 --) νmax (film): 2940,2870,2790 (CH); 1760, 1740(C=O); 1200, 1170 (--C--O--C) cm-1. m/e 271; C16H33NO2 requires 271. filtered through a filter paper to remove the white solid which formed The filtrate was concentrated to give a liquid product which was chromatographed through a column of silica gel (60-200 mesh) the solvent was removed by a rotary evaporator under reduced pressure

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

Procedure: Dodecyl chloroacetate (5.5 g, 0.021 mol) was dissolved in 20 ml of ether and the resultant solution was cooled in an ice-bath. Dimethylamine (40 ml, 0.1M in ether) was added to the cooled solution of dodecyl chloroacetate. The reaction mixture was stirred at room temperature for two hours, then filtered through a filter paper to remove the white solid which formed. The filtrate was concentrated to give a liquid product which was chromatographed through a column of silica gel (60-200 mesh) using ethyl acetate as the eluent. The purity of the fractions was checked by thin layer chromatography. The pure fractions were combined and the solvent was removed by a rotary evaporator under reduced pressure to afford 5.8 g (100% yield) of dodecyl (N,N-dimethylamino)acetate. 1HNMR(CCl4) δ0.83(3H, t, CH3); 1.20[20 H, s, broad, --(CH2)10 ]; 2.23[6H, s, (CH3)2N--]; 3.0 (2H, s, --CH2 --N); 3.93 (2H, t, J=6 Hz, --OCH2 --). νmax (film): 2940, 2870, 2790 (CH); 1760, 1740(C=O); 1200, 1170 (--C--O --C) cm-1. m/e 271; C16H33NO2 requires 271. filtered through a filter paper to remove the white solid which formed The filtrate was concentrated to give a liquid product which was chromatographed through a column of silica gel (60-200 mesh) the solvent was removed by a rotary evaporator under reduced pressure