Ethyl formate → trans-N-[2-(Dimethylamino)-cyclohexyl]-formamide

HRID 262265Notes

Reaction equation

HRID 262265 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].[CH:11](OCC)=[O:12]>>[CH3:1][N:2]([CH3:10])[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][CH:11]=[O:12]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine

Product 1

HCID 13544012trans-N-[2-(Dimethylamino)-cyclohexyl]-formamideYield 85%

Procedure

A solution of the trans 2-(dimethylamino)cyclohexylamine prepared as in Procedure VIII (5.12 g.; 0.036 mole) and 100 ml. of ethyl formate (distilled over K2CO3) was refluxed for 17 hours and evaporated. The titled product (A) was distilled at 0.1 mm, b.p. 104°, 5.2 g. (85% yield). ir NH 3280, 3040; CH 2930, 2860; N-alkyl 2770; C=O 1670; amide II 1540; other 1450, 1385. nmr in CDCl3 (100 MHz) was in accord. Mass spectrum M+ 170.

Workup

  1. customevaporated
  2. distillationThe titled product (A) was distilled at 0.1 mm, b.p. 104°, 5.2 g

Sources & evidence

ORD record
ord-c9a4613fb3ab4704910c17084e96056b
Source dataset
uspto-grants-1979_05
Patent number
US04153717

Reaction notes

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