Triethylamine → 4-[(3-Chloro-benzoylamino)-methyl]-N-(4-chloro-phenyl)-3,N-dimethyl-benzamide

HRID 220975Notes

Reaction equation

HRID 220975 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].C(N(CC)CC)C.[NH2:18][CH2:19][C:20]1[CH:36]=[CH:35][C:23]([C:24]([N:26]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[CH3:27])=[O:25])=[CH:22][C:21]=1[CH3:37]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:18][CH2:19][C:20]1[CH:36]=[CH:35][C:23]([C:24]([N:26]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[CH3:27])=[O:25])=[CH:22][C:21]=1[CH3:37])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 575552204-Aminomethyl-N-(4-chloro-phenyl)-3,N-dimethyl-benzamide

Product 1

HCID 575553934-[(3-Chloro-benzoylamino)-methyl]-N-(4-chloro-phenyl)-3,N-dimethyl-benzamideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chlorobenzoyl chloride (61 mg, 0.35 mmol) and triethyl-amine (to pH9) were added to a solution of 4-aminomethyl-N-(4-chloro-phenyl)-3,N-dimethyl-benzamide from Example E115.2 (100 mg, 0.35 mmol) in dichloro-methane (5 ml) at room temperature. The mixture was stirred for 1 h then concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane) to give a white solid identified as the title compound (101 mg, 69%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane)
  3. customto give a white solid

Sources & evidence

ORD record
ord-d08a26e8bcec448393610d060baf3eb7
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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