2-(Dimethylamino)ethanol → HCID 13867456, compound

HRID 483476Notes

Reaction equation

HRID 483476 reaction equation
[CH3:1][N:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:10][N:11](C)[CH2:12]CO.C([Sn](=O)CCCC)CCC>>[CH3:1][N:2]([CH2:3][C:4]([O:6][CH2:7][CH2:8][N:11]([CH3:12])[CH3:10])=[O:5])[CH3:9]

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 61221Dibutyltin oxideHCID 118412Glycine, N,N-dimethyl-, ethyl ester

Product 1

HCID 13867456HCID 13867456, compound

Conditions

Temperature
130 °C

Procedure

A mixture of 65.5 g (0.5 mol) of ethyl N,N-dimethylglycinate, 44.6 g (0.5 mol) of N,N-dimethylethanolamine and 0.82 g of dibutyltin oxide was heated at about 130° C. The ethanol by-product was collected in a Dean-Stark trap. When the rate of ethanol evolution and amount of ethanol collected showed that the reaction was essentially complete, the reaction was heated at about 180° C. until ethanol evolution ceased. The liquid product was purified by distillation at reduced pressure to provide 2-(N,N-dimethylamino)ethyl N,N-dimethylaminoacetate.

Workup

  1. customThe ethanol by-product was collected in a Dean-Stark trap
  2. customWhen the rate of ethanol evolution and amount of ethanol collected
  3. temperaturethe reaction was heated at about 180° C. until ethanol evolution
  4. distillationThe liquid product was purified by distillation at reduced pressure

Sources & evidence

ORD record
ord-673900bdeea643e0bd396e17f801d006
Source dataset
uspto-grants-1993_07
Patent number
US05225513

Reaction notes

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