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

HRID 27171

Reaction equation

HRID 27171 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([N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][C:22](O)=[O:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OC(=O)C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][NH:8][C:22](=[O:23])[CH2:21][N:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 735138(Diphenylamino)acetic acid

Product 1

HCID 20460535N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(N,N-diphenylamino)acetamideYield 66.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dimethoxyphenethylamine (8.05 g) and N,N-diphenylglycine (10 g) were heated for 2 hours at 190° C. After cooling, the reaction mixture was dissolved in ethylacetate. The resulting solution was washed with a 5% sodium bicarbonate aqueous solution and water and then dried. The solvent was distilled off from the solution to give crystals of N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(N,N-diphenylamino)acetamide (11.5 g), mp 88° to 93° C.

Workup

  1. temperatureAfter cooling
  2. washThe resulting solution was washed with a 5% sodium bicarbonate aqueous solution and water
  3. customdried
  4. distillationThe solvent was distilled off from the solution

Sources & evidence

ORD record
ord-8ed0f0600b0943299b6dc0d2f792cf0d
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Linked notes

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