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

HRID 419628Notes

Reaction equation

HRID 419628 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([N+:23]([O-])=O)=[CH:6][C:7]([CH3:22])=[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)[CH:9]=1)[CH3:2]>CCOC(C)=O.CO.[Pt]>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:15]2)[C:7]([CH3:22])=[CH:6][C:5]=1[NH2:23])[CH3:2]

Participants

5

Reactant 1

HCID 594525651-[5-(Ethyloxy)-2-methyl-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine

Product 1

HCID 594527752-(Ethyloxy)-5-methyl-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}anilineYield 90%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-[5-(ethyloxy)-2-methyl-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine (33.1 g, 89.0 mmol) in EtOAc (800 mL) and MeOH (200 mL) was added platinum on carbon (sulfided) (17.5 g, 4.47 mmol). The mixture was stirred under H2 (1 atm.) over the weekend. The mixture was filtered through Celite®, washed with DCM, and rotovapped down. The resultant solid was triturated with diethyl ether to provide the title compound of Step G (27.3 g, 80 mmol, 90% yield). 1H NMR (400 MHz, DMSO-d6) δ 6.54 (s, 1H), 6.44 (s, 1H), 4.28 (s, 2H), 3.94 (q, J=6.9 Hz, 2H), 3.11-3.22 (m, 2H), 2.97 (s, 3H), 2.87 (d, J=11.5 Hz, 2H), 2.44-2.56 (m, 2H), 2.06 (s, 3H), 1.59-1.80 (m, 4H), 1.43 (ddd, J=14.2, 7.0, 3.5 Hz, 1H), 1.21-1.36 (m, 5H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed with DCM
  3. customThe resultant solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-4d7b5df09c0c4765873f1ddae3e27be4
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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