Triethylamine → 3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propanamide

HRID 413974Notes

Reaction equation

HRID 413974 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH2:6])=[O:5].[CH3:7][NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1.C(N(CC)CC)C>C(#N)C>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][N:8]([CH3:7])[CH2:2][CH2:3][C:4]([NH2:6])=[O:5])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77039N-MethylhomoveratrylamineHCID 799823-Chloropropanimidic acid

Product 1

HCID 205912053-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propanamideYield 64.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.42 g (60 mmol) 3-Chloropropanamide, 5.85 g (30 mmol) N-methyl-3,4-dimethoxybenzeneethanamine and 7.7 g (75 mmol) triethylamine in 100 ml acetonitrile were stirred under reflux for 18 hours. The reaction mixture was concentrated in vacuo and the residue purified by chromatography on silicagel using methylene chloride/methanol: 92/8 to yield 5.12 g (64.1%) of the desired compound as an orange oil.

Workup

  1. temperatureunder reflux for 18 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue purified by chromatography on silicagel

Sources & evidence

ORD record
ord-7576f1867d214e8bb0dc67e7f6ca110c
Source dataset
uspto-grants-2003_05
Patent number
US06570037B2

Reaction notes

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