Water → 1-(6-Chloro-5-trifluoromethylpyridin-2-yl)piperidin-4-yl-carbamic acid tert-butyl ester

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A stirred mixture of D7 (5.0 g, 25 mmol), 2,6-dichloro-3-trifluoromethyl-pyridine (5.4 g, 25 mmol) and cesium carbonate (12.22 g, 37.5 mmol) in 1,4-dioxane (75 mL) was heated at reflux under argon for 64 h. To the mixture, which was cooled to ambient temperature, was added water (250 mL) and DCM (250 mL) with shaking and the layers were separated. The aqueous phase was further extracted with DCM (250 mL) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo to an oil. This material was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane to afford the title compounds

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