[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[CH3:15][NH:16][CH3:17].[C-:18]#[N:19].[Na+].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:16]([CH3:17])[CH3:15])[C:18]#[N:19])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1A mixture of 1-(4-chlorophenyl)cyclobutanecarbaldehyde (13.7 g), dry dimethylamine hydrochloride (6.6 g) and dry dimethylsulphoxide (50 ml) was added dropwise to a stirred mixture of sodium cyanide (3.9 g) in dry dimethylsulphoxide (100 ml). The mixture was stirred for 66 hours at ambient temperature and the reaction mixture was poured into water. The mixture was extracted with ether and the ether solution was then extracted with dilute hydrochloric acid. The aqueous phase was basified and extracted with ether. Removal of the ether gave 2-[1-(4-chlorophenyl)cyclobutyl]-2-dimethylaminoacetonitrile (m.p. 90°-91° C.).
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