Aniline → 1-Phenylamino-cyclohexanecarbonitrile

Participants

Reaction Steps

1.4 ml (15.3 mmol) of aniline (starting product 1) are added to a solution of 1.3 ml (12.5 mmol) of cyclohexanone (starting product 2) in 20 ml of acetic acid at 0° C. The solution is stirred for a time and 1.9 ml (14.2 mmol) of trimethylsilyl cyanide are added. The reaction medium is stirred for one night at room temperature. It is then poured gently into an ice-cold ammonium hydroxide solution until the pH is basic and extracted with dichloromethane. The organic phases are collected and washed with water. They are dried over sodium sulfate. The residue is precipitated in dichloromethane and heptane. The solid is filtered and dried. 2.2 g of 1-phenylaminocyclohexanecarbonitrile are obtained in the form of a whitish solid. M.p.=67-9° C., yield=88%.

Provenance & Evidence