trans-{3-Azidomethyl-1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine → trans-{3-Aminomethyl-1-[2-(4-fluorophenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine

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A mixture of crude trans-{3-azidomethyl-1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine (106 mg, 278 μmol) and 10% palladium on charcoal (20 mg) in ethanol (5 mL) was stirred at room temperature under a hydrogen atmosphere. After 1.75 hours, the mixture was filtered through Celite and the solids were rinsed with ethanol. The filtrate was concentrated to provide a gum (98 mg, quantitative). 1H NMR (300 MHz, CDCl3) δ7.33 (m, 5H), 7.15 (m, 2H), 6.98 (t, J=9 Hz, 2H), 3.72 (d, J=13 Hz, 1H), 3.55 (d, J=13 Hz, 1H), 3.07 (m, 2H), 2.9-2.7 (m, 4H), 2.55 (m, 2H), 2.37 (m, 1H), 2.23 (s, 3H), 2.19 (m, 2H), 2.0-1.6 (m, 5H). Mass spec (AP+) m/z 356.2 (M+H+).

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