2-(Dimethylamino)ethanol → 2-(Dimethylamino)ethyl nonanoate

HRID 1414690Notes

Reaction equation

HRID 1414690 reaction equation
[N+](C[C:5](=[O:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])([O-])=O.[CH3:15][N:16]([CH2:18][CH2:19][OH:20])[CH3:17]>C1C=CC=CC=1>[C:5]([O:20][CH2:19][CH2:18][N:16]([CH3:17])[CH3:15])(=[O:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 2834311-nitrodecan-2-one

Product 1

HCID 544093252-(Dimethylamino)ethyl nonanoateYield 72%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In accordance with practice of the process of this invention, ten parts of 1-nitro-2-decanone, 5.0 parts of dimethylaminoethanol, and 110 parts of dry benzene are admitted to a reaction vessel wherein they are refluxed for four hours. At the end of this time, there are distilled off from the reaction mixture 44 parts by weight of benzene solvent and 2.0 parts by weight of nitromethane. The remaining benzene is then distilled at atmospheric pressure and 80° C. Thereafter the residual dark oil is distilled at 106°-110° C, at 2mm Hg to yield 8.2 parts by weight of N,N-dimethylaminoethyl nonanoate, a pale yellow liquid having a boiling point of 106°-110° C/2mm and a refractive index ND24 1.4355. (Yield 72%)

Workup

  1. temperaturewherein they are refluxed for four hours
  2. distillationAt the end of this time, there are distilled off from the reaction mixture 44 parts by weight of benzene solvent and 2.0 parts by weight of nitromethane
  3. distillationThe remaining benzene is then distilled at atmospheric pressure and 80° C
  4. distillationThereafter the residual dark oil is distilled at 106°-110° C, at 2mm Hg

Sources & evidence

ORD record
ord-110a62c8074145fe95e03f47a5555d65
Source dataset
uspto-grants-1977_01
Patent number
US04002569

Reaction notes

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