Sulfuric Acid → 4-(3-(4-(Azido(cyclopentyl)(phenyl)methyl)piperidin-1-yl)propoxy)benzonitrile

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Reaction Steps

A CHCl3 (4.78 mL, 0.25 M) solution of 4-(3-(4-(cyclopentyl(hydroxy)(phenyl)methyl)piperidin-1-yl)propoxy)benzonitrile (0.5 g, 1.19 mmol) and sodium azide (1.16 g, 17.9 mmol) was cooled to 0° C. To the solution H2SO4 was added dropwise (0.28 mL, 9.3 mmol). The mixture was allowed to warm to rt over 4 h with stirring, then re-cooled to 0° C. and treated with NH4OH till pH was basic. The biphasic solution was extracted with DCM (3×) and the organic layers combined and dried over MgSO4. Concentration under reduced pressure and drying in vacuo afforded a crude oil. Purification by flash chromatography (DCM, MeOH, NH4OH) afforded 4-(3-(4-(azido(cyclopentyl)(phenyl)methyl)piperidin-1-yl)propoxy)benzonitrile (45 mg, 10%): LC-MS (>98%) m/z=444.3 [M+H].

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