Ethyl cyanoacetate → 2-cyano-N-(cyclohexylmethyl)acetamide

HRID 1955636Notes

Reaction equation

HRID 1955636 reaction equation
[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[CH:9]1([CH2:15][NH2:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>>[C:1]([CH2:3][C:4]([NH:16][CH2:15][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:6])#[N:2]

Participants

3

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 76688Cyclohexanemethylamine

Product 1

HCID 190713252-cyano-N-(cyclohexylmethyl)acetamideYield 93.1%

Procedure

2-Cyano-N-(cyclohexylmethyl)acetamide was prepared by the method of V. Papesh, J. Org. Chem. 1951, 16, 1879-1889. Ethyl cyanoacetate (Aldrich, 18.41 mL, 173 mmol) was added to neat cyclohexanemethylamine (Aldrich, 19.585 g, 173 mmol), and the resulting solution was stirred for 2 h under nitrogen. At this time, the reaction mixture solidified. After standing for 18 h the white crystalline solid was broken up, filtered, washed with water (150 mL), and dried (0.1 Torr, 40° C.) to provide 2-cyano-N-(cyclohexylmethyl)acetamide (29.030 g, 93%), m.p. 83°-84° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. custom2-Cyano-N-(cyclohexylmethyl)acetamide was prepared by the method of V
  2. waitAfter standing for 18 h
  3. filtrationfiltered
  4. washwashed with water (150 mL)
  5. customdried (0.1 Torr, 40° C.)

Sources & evidence

ORD record
ord-246ab1a9a25b4f8b8f7a9b88af806256
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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