Phenethylamine → 2-(3,4-dimethoxyphenyl)-N-(2-phenylethyl)acetamide

HRID 1108904Notes

Reaction equation

HRID 1108904 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27]1([CH2:33][CH2:34][NH2:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([NH:35][CH2:34][CH2:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 2972462-(3,4-dimethoxyphenyl)-N-(2-phenylethyl)acetamideYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3,4-dimethoxyphenylacetic acid (17.1 g, 0.090 mol) and carbonyldimidazole (14.6 g, 0.090 mol) in THF (200 ml) was stirred for 2.5 h in a flask fitted with a drying tube. To this solution was added 2-phenylethylamine (10.9 g, 0.090 mol) in THF (50 ml). After 1 h the THF was evaporated and the residue was treated with water (200 ml) and filtered. The crude amide was washed with water and recrystallized from mixture of 200 ml of methanol and 100 ml of water with a charcoal treatment to afford 21.6 g (80.3%) of the title compound mp 123°-124°. A second crop (2.1 g, (7.8%) was obtained after concentrating the mother liquors.

Workup

  1. customfitted with a drying tube
  2. customAfter 1 h the THF was evaporated
  3. additionthe residue was treated with water (200 ml)
  4. filtrationfiltered
  5. washThe crude amide was washed with water
  6. customrecrystallized from mixture of 200 ml of methanol and 100 ml of water with a charcoal treatment

Sources & evidence

ORD record
ord-33f955048ab24bebadfa5ce8f39ca019
Source dataset
uspto-grants-1994_06
Patent number
USRE034630

Reaction notes

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