Dibenzylamine → 2-[bis(phenylmethyl)amino]-N-(2-methoxyphenyl)acetamide

HRID 463719Notes

Reaction equation

HRID 463719 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])=[O:4].[CH2:14]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[C:15]1([CH2:14][N:21]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH3:13])=[O:4])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 416472-Chloro-N-(2-methoxyphenyl)acetamide

Product 1

HCID 135605532-[bis(phenylmethyl)amino]-N-(2-methoxyphenyl)acetamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 28.1 g of 2-chloro-N-(2-methoxyphenyl)acetamide (C.A. 50, 8730i) in 200 ml toluene was added 58.3 g of dibenzylamine and refluxed for 48 hours. After separation of dibenzylamine hydrochloride, the solvent was removed from the reaction mixture. Crystallization of the residue from isopropylether gave 41.9 g colorless crystals of 2-[bis(phenylmethyl)amino]-N-(2-methoxyphenyl)acetamide, mp 92°-94°.

Workup

  1. temperaturerefluxed for 48 hours
  2. customAfter separation of dibenzylamine hydrochloride
  3. customthe solvent was removed from the reaction mixture
  4. customCrystallization of the residue from isopropylether

Sources & evidence

ORD record
ord-c24279feb3d043638f127fce00c6df15
Source dataset
uspto-grants-1985_10
Patent number
US04544657

Reaction notes

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