Ammonium formate → 4-(4-Benzofuranyl)-piperidine

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Reaction Steps

A stirred mixture of 4-(4-benzofuranyl)-1,2,3,6-tetrahydro-pyridine hydrochloride [CAS-No. 158984-66-8] (2.05 g, 8.7 mmol), prepared from commercially available 4-bromo-benzofurane [CAS-No. 128868-60-0] and commercially available tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate, palladium on carbon (10%, 0.46 g, 0.44 mmol), ammonium formate (2.74 g, 43.5 mmol) and MeOH (79 ml) was heated at reflux conditions for 1 h, cooled to RT, filtrated and evaporated. Saturated sodium bicarbonate solution (50 ml) was added to the residue, and the inorganic layer was extracted with dichloromethane (2×40 ml). The combined organic layers were washed with brine (40 ml), dried (MgSO4) and evaporated to yield 4-(4-benzofuranyl)-piperidine as a colorless oil (1.65 g, 94%), MS (ISP) m/z=202.3 [(M+H)+].

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