Veratrylamine → N-(3-Chlorophenyl)-2-[[(3,4-dimethoxyphenyl)methyl]amino]acetamide

Reaction equation

Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)=[O:4].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][NH2:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>>[Cl:12][C:8]1[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:24][CH2:23][C:17]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:15]([O:14][CH3:13])[CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 79832Veratrylamine

HCID 5322122-bromo-N-(3-chlorophenyl)acetamide

Product 1

HCID 14998797N-(3-Chlorophenyl)-2-[[(3,4-dimethoxyphenyl)methyl]amino]acetamide

Procedure

In a manner similar to Preparation 11, react 2-bromo-N-(3-chlorophenyl)acetamide (4.4 g, 18 mmol) with 3,4-dimethoxybenzenemethanamine (8.7 g, 53 mmol) to obtain the title compound.

Workup

customIn a manner similar to Preparation 11

Sources & evidence

ORD record: ord-b450f8a96375490dbad5101337b4567c
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051422

Reaction notes

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