Phenethylamine → 3,4-dimethoxy-N-(2-phenylethyl)benzamide

HRID 1031899Notes

Reaction equation

HRID 1031899 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:26]1([CH2:32][CH2:33][NH2:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([NH:34][CH2:33][CH2:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:8]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 7121Veratric AcidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 8193303,4-dimethoxy-N-(2-phenylethyl)benzamideYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3,4-dimethoxybenzoic acid (9.1 g, 0.05 mol) and carbonyldiimidazole (8.1 g, 0.05 mol) in 100 ml of THF was stirred for 3 h protected from moisture. The resulting solution was treated with 2-phenylethylamine (6.1 g, 0.05 mol) dissolved in 10 ml of THF. After 2 h of stirring, the solvent was evaporated and the solid residue was washed with dilute NaOH, dilute HCl, and water. The crude Al was recrystallized from 75 ml of EtOH to afford 9.35 g (57%) of N-(3,4-dimethoxybenzoyl)-2-phenylethylamine, mp 123-124°.

Workup

  1. customthe solvent was evaporated
  2. washthe solid residue was washed with dilute NaOH, dilute HCl, and water
  3. customThe crude Al was recrystallized from 75 ml of EtOH

Sources & evidence

ORD record
ord-0613482e43c74beeac06e7060a93b684
Source dataset
uspto-grants-1990_09
Patent number
US04956371

Reaction notes

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