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

HRID 1601336Notes

Reaction equation

HRID 1601336 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 (30mmol) 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-a2f2ec92e596457285de2ba5841167b7
Source dataset
uspto-grants-1999_11
Patent number
US05977179

Reaction notes

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