Dimethylamine → Dodecyl N,N-dimethylglycinate

HRID 1090725Notes

Reaction equation

HRID 1090725 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:4].[CH3:18][NH:19][CH3:20]>CCOCC>[CH3:18][N:19]([CH2:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:4])[CH3:20]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 228182Dodecyl chloroacetate2×

Product 1

HCID 129378Dodecyl N,N-dimethylglycinateYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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.

Workup

  1. filtrationfiltered through a filter paper
  2. customto remove the white solid which
  3. customformed
  4. concentrationThe filtrate was concentrated
  5. customto give a liquid product which
  6. customwas chromatographed through a column of silica gel (60-200 mesh)
  7. customthe solvent was removed by a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-1f3e971581e3411fb577b6147559207b
Source dataset
uspto-grants-1992_01
Patent number
US05082866

Reaction notes

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