2-((4-Chlorophenyl)amino)acetic acid → N-[2-(3,4-dibenzyloxyphenyl)ethyl]-2-(p-chloroanilino)acetamide

HRID 27168Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][CH2:13][NH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:37]=[CH:36][C:30]([NH:31][CH2:32][C:33](O)=[O:34])=[CH:29][CH:28]=1>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][CH2:13][NH:14][C:33](=[O:34])[CH2:32][NH:31][C:30]2[CH:36]=[CH:37][C:27]([Cl:26])=[CH:28][CH:29]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 3,4-dibenzyloxyphenethylamine (36.2 g) and p-chloroanilinoacetic acid (20 g) was stirred for 3 hours at 190° C. The reaction mixture was dissolved in benzene. The solution was washed with a diluted potassium carbonate aqueous solution and dried. The solvent was distilled off from the benzene solution and the residue obtained was purified by column chromatography on silica gel to give N-[2-(3,4-dibenzyloxyphenyl)ethyl]-2-(p-chloroanilino)acetamide (27.2 g), mp 121° C.

Workup

washThe solution was washed with a diluted potassium carbonate aqueous solution
customdried
distillationThe solvent was distilled off from the benzene solution
customthe residue obtained
customwas purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-d32a625541c54a508541c94c4e741306
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220647

Reaction notes

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