Aniline → 1-(Phenylamino)cyclopentanecarbonitrile

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=O)[CH2:12][CH2:11][CH2:10][CH2:9]1.C[Si]([C:18]#[N:19])(C)C>C(O)(=O)C>[C:2]1([NH:1][C:8]2([C:18]#[N:19])[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Procedure

2.9 ml (31.8 mmol) of aniline (starting product 2) are added to a solution of 2.6 ml (29.4 mmol) of cyclopentanone (starting product 3) in 30 ml of acetic acid at 0° C. The solution is stirred for 15 minutes and 4 ml (30 mmol) of trimethylsilyl cyanide are added. The reaction medium is stirred for one night at room temperature and then gently poured into an ice-cold ammonium hydroxide solution while keeping the pH basic and extracted with dichloromethane. The organic phases are collected and washed with water. They are dried over sodium sulfate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 90/10, v/v). 5 g of 1-phenylaminocyclopentanecarbonitrile are obtained in the form of a clear brown oil. Yield=91%.