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

Participants

Reaction Steps

To 1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine (26 g, 73 mmol) in EtOAc (1 L) and MeOH (200 mL) was added platinum on carbon (sulfided) (14 g, 73 mmol) as a slurry in EtOAc (100 mL). The mixture was stirred under H2 (1 atm.) for 2 days. The catalyst was filtered off and rinsed with EtOAc, MeOH, and DCM and the filtrate was rotovapped down. The resultant solid was triturated with diethyl ether to provide the title compound of Step J (20 g, 61 mmol, 82%). 1H NMR (400 MHz, DMSO-d6) δ 6.50 (s, 1H), 6.39 (s, 1H), 4.24 (s, 2H), 3.66 (s, 3H), 3.05-3.16 (m, 2H), 2.92 (s, 3H), 2.83 (d, 2H), 2.39-2.54 (m, 2H), 2.01 (s, 3H), 1.55-1.76 (m, 4H), 1.32-1.46 (m, J=10.6, 7.0, 3.5, 3.5 Hz, 1H), 1.24 (qd, J=11.7, 3.4 Hz, 2H).

Provenance & Evidence