Acetyl chloride → trans-N-[2-(N,N-dimethylamino)cyclohexyl]acetamide

HRID 26260Notes

Reaction equation

HRID 26260 reaction equation
[CH3:1][N:2]([CH3:10])[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH2:9].[C:11](Cl)(=[O:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>>[CH3:1][N:2]([CH3:10])[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:11](=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine

Product 1

HCID 11735567trans-N-[2-(N,N-dimethylamino)cyclohexyl]acetamide

Procedure

This amide was prepared by general procedure A from trans-2-(dimethylamino)cyclohexylamine and acetyl chloride. In the work up the aqueous layer was salted out with solid K2CO3, and extracted well with ether. The resulting oil was crystallized from ether-petroleum ether (30°-60°) to give colorless rods of the sub-titled amide, 79% yield, m.p. 86°-87.5° raised to 88°-89° on recrystallization. ir NH 3280, 3080; N-alkyl 2770; C=O 1660, 1640; amide II 1565. nmr in CDCl3 and 100 MHz was in accord. Mass spectrum M+ 184.

Workup

  1. extractionextracted well with ether
  2. customThe resulting oil was crystallized from ether-petroleum ether (30°-60°)

Sources & evidence

ORD record
ord-2a2510b7c17045cab93fdfe78cb15e3b
Source dataset
uspto-grants-1979_04
Patent number
US04148914

Reaction notes

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