Potassium Carbonate → 2-chloro-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine

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A To a mixture of 2-chloro-4-(4-hydroxyphenyl)pyridine hydrobromide (593 m g) and potassium carbonate (1.66 g) in N,N-dimethylformamide (15 mL) heated at a temperature close to 65° C. is added (3S)-1-(3-methane-sulfonyloxypropyl)-3-methylpiperidine hydrochloride (625 mg). The mixture is heated at a temperature close to 65° C. for six hours, allowed to cool back to room temperature and filtered. The precipitate is washed with N,N-dimethylformamide and the organic phases are concentrated under reduced pressure. The residue is purified by column chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 90/10) to afford 434 mg of 2-chloro-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine as an orange oil. Conversion to the oxalate is performed by mixing the crude base (87 mg) and oxalic acid (46 mg) in a mixture of ethanol and diethyl ether. Filtration of the insoluble and drying under reduced pressure gives 82 mg of 2-chloro-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine, dioxalate as an off white solid melting at 143° C.

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