Benzoyl chloride, 3-chloro- → trans-m-Chloro-N-[2-(dimethylamino)cyclohexyl]-benzamide

HRID 1701381Notes

Reaction equation

HRID 1701381 reaction equation
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[NH2:9].[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=[O:16]>>[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH:9][C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:3]1[N:2]([CH3:10])[CH3:1])=[O:16]

Participants

3

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 12447266N1,N1-dimethylcyclohexane-1,2-diamine

Product 1

HCID 53979363trans-m-Chloro-N-[2-(dimethylamino)cyclohexyl]-benzamideYield 62%

Procedure

This titled amide was prepared by general procedure B from 2-(dimethylamino)cyclohexylamine and 3-chlorobenzoyl chloride. The crude product was crystallized from ether-petroleum ether (30°-60°); yield 62%, m.p. 112°-113°. The analytical sample melted at 112.5°-113.5°. uv sh 217 nm (ε 11,850); sh 226 (9,550); sh 277 (1,200); sh 287 (623). ir NH/=CH 3320, 3070; N-alkyl 2760; C=O 1635; C=C 1595, 1570; amide II 1545. NMR in CDCl3 (100 MHz) was in accord. Mass specrum M+ 280.

Workup

  1. customThe crude product was crystallized from ether-petroleum ether (30°-60°)

Sources & evidence

ORD record
ord-73917e1158d74b268c9134938d67abef
Source dataset
uspto-grants-1980_03
Patent number
US04192885

Reaction notes

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