Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#N)=[CH:13][CH:12]=1.[Cl-].[NH4+].[OH2:21]>O1CCCC1>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]([CH:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)=[O:21])=[CH:13][CH:12]=1To a stirred and cooled (10°-15° C.) Grignard-complex, previously prepared starting from 13.5 parts of 4-chloro-1-methylpiperidine and 2.4 parts of magnesium in 68 parts of tetrahydrofuran, is added dropwise a solution of 10 parts of 4-bromobenzonitrile in 22 parts of tetrahydrofuran. Upon completion, stirring is continued for 1 hour at reflux temperature. The reaction mixture is decomposed by pouring onto a mixture of 50 parts of ammonium chloride in 250 parts of water. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 10 parts of (4-bromophenyl)-(1-methyl-4-piperidinyl)methanone as a residue.
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