1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine → 5-Methyl-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}aniline
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:15][CH2:14]1>CCOC(C)=O.[Pt]>[CH3:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][S:21]([CH3:24])(=[O:22])=[O:23])[CH2:15][CH2:14]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]Participants
4
Procedure
To 1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine (3.26 g, 9.14 mmol) in EtOAc (100 mL) was added platinum on carbon (sulfided) (1.77 g, 0.460 mmol). The mixture was stirred under H2 (1 atm.) overnight. Filtering the mixture through Celite® and concentrating provided the title compound of Step E (1.77 g, 5.42 mmol, 59%). 1H NMR (400 MHz, DMSO-d6) δ 6.55 (s, 1H), 6.43 (s, 1H), 4.29 (s, 2H), 3.71 (s, 3H), 3.10-3.19 (m, 2H), 2.97 (s, 3H), 2.88 (d, 2H), 2.51-2.58 (m, 2H), 2.06 (s, 3H), 1.61-1.79 (m, 4H), 1.19-1.52 (m, 3H).