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

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Reaction Steps

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.

Provenance & Evidence