trans-1-{4-(Benzyl-methylamino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea → trans-1-{4-Methylamino-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea

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A solution of trans-1-{4-(benzyl-methylamino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea (95 mg, 162 μmol) in methanol (20 mL) was combined with Pearlman's catalyst (20% palladium hydroxide on charcoal, 100 mg) and shaken under a hydrogen atmosphere (60 psig) for 15 hours. The mixture was filtered through Celite and the solids were washed with methanol. The filtrate was concentrated under vacuum to provide a pale tan solid (78 mg, 97%). 1H NMR (300 MHz, CDCl3) δ7.78 (s, 1H), 7.36 (s, 1H), 7.16 (m, 2H), 7.13 (s, 1H), 6.96 (t, J=9 Hz, 2H), 4.14 (s, 3H), 3.66 (m, 1H), 3.4-3.1 (m, 4H), 2.95 (s, 3H), 2.9-2.3 (m, 12H), 2.18 (m, 2H), 1.22 (t, J=8 Hz, 3H). Mass spec (ES+) m/z 495.2 (M+H+).

Provenance & Evidence