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

HRID 419615Notes

Reaction equation

HRID 419615 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

Reactant 1

HCID 594526541-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine

Product 1

HCID 594526535-Methyl-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}anilineYield 59.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

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).

Workup

  1. filtrationFiltering the mixture through Celite®
  2. concentrationconcentrating

Sources & evidence

ORD record
ord-7ee2202c85324d8399364ca45b82ed04
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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