1-[2-Ethyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine → 5-Ethyl-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}aniline

Participants

Reaction Steps

To 1-[2-ethyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine (0.25 g, 0.68 mmol) in EtOAc (30 mL) was added platinum on carbon (sulfided) (0.13 g, 0.034 mmol). The mixture was stirred under H2 (1 atm.) overnight. Filtering the mixture through Celite® and concentrating provided the title compound of Step B (0.18 g, 0.54 mmol, 79%). 1H NMR (400 MHz, DMSO-d6) δ 6.55 (s, 1H), 6.42 (s, 1H), 4.30 (br. s., 2H), 3.67 (s, 3H), 3.04-3.16 (m, 2H), 2.92 (s, 3H), 2.77 (d, J=11.5 Hz, 2H), 2.52 (t, J=10.9 Hz, 2H), 2.38-2.44 (m, 2H), 1.56-1.75 (m, 4H), 1.39 (ddd, J=10.7, 7.1, 3.5 Hz, 1H), 1.24 (qd, J=11.7, 3.2 Hz, 2H), 1.04 (t, J=7.6 Hz, 3H).

Provenance & Evidence