Ammonium formate → 4-(Benzofuran-3-yl)-piperidine

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Reaction Steps

A stirred mixture of 4-(benzofuran-3-yl)-1,2,3,6-tetrahydropyridine hydrochloride (1.57 g, 6.66 mmol), palladium on carbon (10%, 0.35 g, 0.33 mmol), ammonium formate (2.1 g, 33 3 mmol) and MeOH (61 ml) was heated at reflux conditions for 1 h, cooled to RT, filtrated and evaporated. The residue was diluted with ice-water (20 ml) and 3M NaOH (10 ml) and extracted with dichloromethane/methanol 9:1 (4×50 ml). The combined organic layers were washed with brine (1×25 ml), dried (MgSO4) and evaporated. The crude product (1.37 g) was purified by flash chromatography on silica gel (dichloromethane/methanol/NH4OH 65:10:1) to yield 4-(benzofuran-3-yl)-piperidine as a light yellow oil (1.1 g, 82%), MS (ISP) m/z=202.3 [(M+H)+].

Provenance & Evidence