Ethyl formate → N-(4-dimethylaminobutyl)formamide

HRID 927965Notes

Reaction equation

HRID 927965 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH:9](OCC)=[O:10]>>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH:9]=[O:10]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 770634-Dimethylaminobutylamine

Product 1

HCID 54572491N-(4-dimethylaminobutyl)formamide

Procedure

A solution of 4-dimethylaminobutylamine (3.0 g) in ethyl formate (30 mL) was stirred and heated at reflux under an atmosphere of nitrogen for 3 hours. After cooling, the mixture was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM (20%) to give N-(4-dimethylaminobutyl)formamide (2.7 g) as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux under an atmosphere of nitrogen for 3 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of methanol and DCM (20%)

Sources & evidence

ORD record
ord-80c57ad9e6fd47408c1b2686fd0f3111
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

Loading…