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

HRID 419602Notes

Reaction equation

HRID 419602 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:16][CH2:15]1)[CH3:2]>CCOC(C)=O.[Pt]>[CH2:1]([C:3]1[C:4]([N:14]2[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:19]2)=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:8]=1)[NH2:9])[CH3:2]

Participants

4

Reactant 1

HCID 594528971-[2-Ethyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine

Product 1

HCID 594528395-Ethyl-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}anilineYield 79.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  1. filtrationFiltering the mixture through Celite®
  2. concentrationconcentrating

Sources & evidence

ORD record
ord-e110db68dd40405d89866efdfcb11636
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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