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

HRID 419605Notes

Reaction equation

HRID 419605 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

Reactant 1

HCID 594526821-[2-Ethyl-5-(ethyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine

Product 1

HCID 594526665-Ethyl-2-(ethyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}anilineYield 98.2%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

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).

Workup

  1. filtrationFiltering the mixture through Celite®
  2. concentrationconcentrating

Sources & evidence

ORD record
ord-f40b43a6ec414cbe8aeda586953fd843
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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