Ethanol → 1-(4-Aminophenyl)-4-piperidinemethanol

Participants

Reaction Steps

Into a Round bottom flask, [A] [1-(4-Nitro-phenyl)-piperidin-4-yl]-methanol (5.021 g, 0.02125 mol), Ethanol (150 mL, 2.6 mol) and 10% Pd/C (10:90, Palladium:carbon black, 2.3 g, 0.0021 mol). The mixture was evacuated and charged with hydrogen via a balloon (3×). The reaction was stirred at RT under an atmosphere of Hydrogen over night. The solid was filtered and washed with Ethanol. The solvent was removed under vacuum to give [1-(4-Amino-phenyl)-piperidin-4-yl]-methanol a brown solid. The solid was triturated with Et2O to give a pink solid. NMR 1H (DSMO-d6)-6.68 (d, 2H, J=8.72 Hz), 6.47 (d, 2H J=8.68 Hz), 4.51 (bs, 2H), 4.43 (t, 1H, J=4.25 Hz), 3.22-3.40 (m, 4H), 2.43 (dt, 2H, JJ=2.24, 9.61 Hz) 1.70 (bd, 2H, J=11.15 Hz), 1.25-1.47 (m, 3H)

Provenance & Evidence