Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12](=[O:20])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cu](C#N)[C:22]#[N:23].O.N>N1C=CC=CC=1>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12](=[O:20])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[N:23]To 8.55 g of 6-(4-chlorophenyl)-1-phenyl-2-piperidone were added 5.58 g of copper cyanide and 14 ml of pyridine, and the mixture was heated with stirring at 240° C. for 19 hours. The mixture was treated with diluted ammonia water, and then extracted with ethyl acetate. The extracts were washed with water, dried and treated with activated charcoal. After removal of charcoal and the solvent, the residue was purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1 to 3), and recrystallized from a mixture of ethyl acetate and isopropyl ether to give 3.48 g of 6-(4-cyanophenyl)-1-phenyl-2-piperidone as pale yellow prisms.
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