[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1>[Pd].C(O)C>[NH2:17][C:16]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:2][CH3:1]Into a par bottle, 1-(3-Methoxy-4-nitro-benzyl)-piperidin-4-ol (0.74 g, 2.8 mmol), Ethanol (20 mL) and 10% Pd/C (10:90, Palladium:carbon black, 0.30 g, 0.28 mmol) were added. The reaction mixture was evacuated and charged with hydrogen at 35 psi. The mixture was shaken for 3 hours. The solid was filtered through Celite and washed with methanol. The solvent was removed under vacuum to give 1-(4-Amino-3-methoxy-benzyl)-piperidin-4-ol as a semi-solid.
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