1-(1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine → 2-Methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 206a (6.88 g, 20.57 mmol) in a mixture of methanol (180 mL) and dichloromethane (20 mL) was added Raney nickel (50% in water, 3 g). This suspension was purged with hydrogen and stirred under hydrogen of 40 psi at 50° C. for 6 hours. Solid material was removed, and the filtrate was concentrated to provide the title product. Yield: 100%. MS (DCI) m/z 305 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ 1.47-1.59 (m, 2H), 1.84 (d, J=11.87 Hz, 2H), 2.33 (s, 3H), 2.44-2.71 (m, 12H), 3.28-3.48 (m, J=12.21 Hz, 4H), 3.73 (s, 2H), 6.29 (dd, J=8.31, 2.54 Hz, 1H), 6.46-6.54 (m, 2H).

Provenance & Evidence