trans-3-Azidomethyl-1-[2-(4-fluorophenyl)-ethyl]-4-methylpiperidine → trans-1-[2-(4-Fluorophenyl)ethyl]-4-methyl-piperidin-3-ylmethylamine

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A mixture of trans-3-azidomethyl-1-[2-(4-fluorophenyl)-ethyl]-4-methylpiperidine (252 mg, 911 μmol) and 10% palladium on charcoal (90 mg) in ethanol (25 mL) was shaken under a hydrogen atmosphere (60 psig) for 4 hours. The mixture was filtered and the filtrate was concentrated under vacuum to provide a sticky solid (226 mg, quantitative). 1H NMR (300 MHz, CDCl3) δ7.16 (m, 2H), 6.97 (t, J=9 Hz, 2H), 3.12 (m, 1H), 2.98 (m, 1H), 2.93 (dd, J=13, 3 Hz, 1H), 2.80 (m, 2H), 2.58 (m, 3H), 1.99 (m, 1H), 1.80 (m, 1H), 1.8-1.6 (m, 3H), 1.5-1.1 (m, 3H), 0.97 (d, J=6 Hz, 3H). Mass spec (ES+) m/z 251.1 (M+H+, 100%).

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