C(N1CCC(C)(O)CC1)C1C=CC=CC=1.[Cl-:16].[Cl-].[Cl-].[Al+3].[OH-].[Na+].[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:36]2[CH:41]=[CH:40][C:39](Cl)=[CH:38][CH:37]=2)([CH3:35])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClC1C=CC=CC=1>[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[Cl:16])([CH3:35])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=11-Benzyl-4-methyl-piperidin-4-ol (4.5 g) was dissolved in chlorobenzene (50 mL). Aluminium trichloride (15 g) was added portion wise and the mixture then heated at reflux for 0.5 hours. The mixture was then allowed to cool and poured over ice. The resulting solution was treated with sodium hydroxide until basic and the products extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by silica chromatography eluting with a mixture of ethyl acetate and hexane. The fractions containing the desired products were combined and the solvent removed by evaporation to give a 4:1 mixture of the title compound and 1-benzyl-4-(4-chloro-phenyl)-4-methyl-piperidine which was used directly without further purification.
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