1-[2-Ethyl-5-(ethyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine → 5-Ethyl-2-(ethyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}aniline
Reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][CH2:13][CH3:14])=[CH:5][C:4]=1[N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:17][CH2:16]1)[CH3:2]>[Pt]>[CH2:1]([C:3]1[C:4]([N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:17][CH2:16]2)=[CH:5][C:6]([O:12][CH2:13][CH3:14])=[C:7]([CH:8]=1)[NH2:9])[CH3:2]Participants
3
Procedure
To 1-[2-ethyl-5-(ethyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine (0.22 g, 0.57 mmol) in EtOAC (30 mL) was added platinum on carbon (sulfided) (0.11 g, 0.029 mmol). The mixture was stirred under H2 (1 atm) overnight. Filtering the mixture through Celite® and concentrating provided the title compound of Step C (0.21 g, 0.56 mmol, 98%). 1H NMR (400 MHz, DMSO-d6) δ 6.55 (s, 1H), 6.44 (s, 1H), 4.29 (br. s., 2H), 3.91 (q, J=7.1 Hz, 2H), 3.02-3.21 (m, 2H), 2.94 (s, 3H), 2.78 (d, J=11.2 Hz, 2H), 2.37-2.59 (m, 6H), 1.57-1.77 (m, 3H), 1.34-1.49 (m, 1H), 1.18-1.34 (m, 4H), 1.05 (t, J=7.5 Hz, 3H).