{1-[2-(4-Fluorophenyl)ethyl]-piperidin-3-ylmethyl}carbamic Acid Benzyl Ester → C-{1-[2-(4-Fluorophenyl)ethyl]-piperidin-3-yl}methylamine
Reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:13]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][N:14]2[CH2:15][CH2:16][CH2:17][CH:12]([CH2:11][NH2:10])[CH2:13]2)=[CH:21][CH:22]=1Participants
4
Procedure
A solution of {1-[2-(4-fluorophenyl)ethyl]-piperidin-3-ylmethyl}carbamic acid benzyl ester (140 mg, 370 μmol) was combined with Pearlman's catalyst (50 mg) and methanol (10 mL) and shaken under an atmosphere of hydrogen (40 psig) for 17 hours. The mixture was filtered, and the filtrate was concentrated to provide a gum (88 mg, quantitative) which was used without further purification. 1H NMR (300 MHz, CD3OD) δ7.21 (m, 2H), 6.99 (t, J=9 Hz, 2H), 3.1-2.9 (m, 2H), 2.80 (m, 2H), 2.60 (m, 2H), 2.1-1.0 (m, 9H).