Methanol → 1-{4-[1-(4-Amino-3-methoxyphenyl)piperidin-4-yl]piperazin-1-yl}ethan-1-one

Participants

Reaction Steps

NaBH4 (0.190 g, 5.06 mmol) was added carefully in portions (exothermic) to a suspension of 1-acetyl-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (0.52 g, 1.45 mmol), nickel(II)chloride hexahydrate (0.170 g, 0.72 mmol), MeOH (8 mL) and THF (4 mL) at 0° C. The ice bath was removed and the reaction mixture was stirred at rt overnight (˜16 h). The solvent was evaporated and the residue was suspended in DCM and filtered through celite. Flash chromatography afforded the title compound of step B (0.36 g, 76%). 1H NMR (400 MHz, DMSO-d6) δ 6.50-6.45 (m, 2H), 6.30-6.25 (m, 1H), 4.18 (bs, 2H), 3.71 (s, 3H), 3.45-3.36 (m, 6H), 2.45-2.38 (m, 3H), 2.31-2.23 (m, 1H), 1.96 (s, 3H), 1.82-1.74 (m, 2H), 1.58-1.44 (m, 2H).

Provenance & Evidence