p-Toluidine → 1-p-Tolylaminocyclohexanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

10 g of cyclohexanone (101.9 mmol, 1 eq.) (starting material 1) are dissolved in 150 ml of acetic acid (15 vol.) in a 500 ml three-necked flask, at room temperature and under nitrogen, the mixture is cooled in an ice bath (10° C.) and followed by portionwise addition of 13.1 g of para-toluidine (starting material 2) (122.3 mmol, 1.2 eq.), and the mixture is then stirred for 15 minutes at 10° C. 15 ml (112.1 mmol, 1.1 eq.) of trimethylsilyl cyanide are then introduced. The reaction medium is stirred overnight at room temperature. It is then poured gently into ice-cold 20% ammonium hydroxide solution (300 ml) until the pH is basic, and extracted with 300 ml of dichloromethane. The aqueous phase is again extracted with 200 ml of dichloromethane. The organic phases are combined and washed with 400 ml of water and then dried over magnesium sulfate. After evaporation, the residue is triturated in heptane, and the product 1-p-tolylaminocyclohexanecarbonitrile is isolated in the form of a white solid.

Provenance & Evidence