Homoveratrylamine → N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(p-toluidino)acetamide

HRID 27164

Reaction equation

HRID 27164 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][NH2:8].[C:14]1([CH3:25])[CH:19]=[CH:18][C:17]([NH:20][CH2:21][C:22](O)=[O:23])=[CH:16][CH:15]=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][NH:8][C:22](=[O:23])[CH2:21][NH:20][C:17]2[CH:18]=[CH:19][C:14]([CH3:25])=[CH:15][CH:16]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 2422362-[(4-Methylphenyl)amino]acetic acid

Product 1

HCID 10042154N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(p-toluidino)acetamideYield 71.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dimethoxyphenethylamine (14.4 g ) and p-toluidinoacetic acid (13.1 g) were heated for 1.5 hours at 190° C. in a stream of nitrogen. After cooling, the reaction mixture was dissolved in ethyl acetate and the solution was washed with a cooled 1 N sodium hydroxide solution and water and then dried. The solvent was distilled off and the oily residue was crystallized by adding ether to give N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(p-toluidino)acetamide (18.6 g), mp 87° to 88.5° C.

Workup

  1. temperatureAfter cooling
  2. washthe solution was washed with a cooled 1 N sodium hydroxide solution and water
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe oily residue was crystallized
  6. additionby adding ether

Sources & evidence

ORD record
ord-e0e102ed6dc546d8920f4a44faf3a4e8
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Linked notes

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