C(O)(=O)C(C1C=CC=CC=1)O.[CH3:12][C@H:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1.Cl[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:35][CH2:34][C:33](=[O:36])[CH2:32][CH2:31]2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[O:36]=[C:33]1[CH2:34][CH2:35][CH:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][CH2:20][N:15]3[CH2:16][CH2:17][CH2:18][C@H:13]([CH3:12])[CH2:14]3)=[CH:29][CH:28]=2)[CH2:31][CH2:32]1A mixture of (3S)-3-methylpiperidine mandelate (1.57 g), 4-[4-(3-chloropropoxy)phenyl]cyclohexanone (1.33 g), potassium carbonate (2.0 g) and a catalytic amount of potassium iodide in N,N-dimethylformamide (20 mL) is stirred overnight at a temperature close to 100° C., cooled back to room temperature and filtrated. The precipitate is rinsed with ethanol, the filtrate concentrated under reduced pressure and purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 90/10). Fractions containing the expected product are pooled and concentrated under reduced pressure to give 1.04 g of (3S)-1-{3-[4-(4-oxocyclohexyl)phenoxy]propyl}-3-methylpiperidine as an orange coloured oil used without further purification.
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