1-(1-(2-Ethyl-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-(methylsulfonyl)piperazine → 5-Ethyl-2-methoxy-4-(4-(4-(methylsulfonyl)piperazin-1-yl)piperidin-1-yl)aniline

HRID 419599Notes

Reaction equation

HRID 419599 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]([N:20]2[CH2:25][CH2:24][N:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[CH2:16][CH2:15]1)[CH3:2]>CCOC(C)=O.[Pt]>[CH2:1]([C:3]1[C:4]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:21][CH2:22][N:23]([S:26]([CH3:29])(=[O:27])=[O:28])[CH2:24][CH2:25]3)[CH2:16][CH2:15]2)=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:8]=1)[NH2:9])[CH3:2]

Participants

4

Reactant 1

HCID 594529781-(1-(2-Ethyl-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-(methylsulfonyl)piperazine

Product 1

HCID 594530035-Ethyl-2-methoxy-4-(4-(4-(methylsulfonyl)piperazin-1-yl)piperidin-1-yl)anilineYield 46%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-{1-[2-ethyl-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine (1.12 g, 2.63 mmol) and sulfided platinum on carbon (0.410 g, 0.105 mmol) in EtOAc (40 mL) was sealed in a round bottom flask with a rubber septum. The reaction mixture was purged with N2 gas and then a balloon of H2 gas was connected and the vessel was flushed with the H2 gas. The reaction was stirred at rt for 2 d. TLC analysis showed the complete consumption of the starting nitro compound so the reaction mixture was filtered through celite to remove the catalyst. The filtrate was concentrated onto silica gel and purified by flash chromatography to afford 5-ethyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (0.479 g, 46%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.60 (s, 1H), 6.46 (s, 1H), 4.35 (br. s., 2H), 3.71 (s, 3H), 3.03-3.16 (m, 4H), 2.81-2.93 (m, 5H), 2.56-2.68 (m, 6H), 2.29-2.42 (m, 1H), 1.72-1.89 (m, 2H), 1.44-1.62 (m, 2H), 1.09 (t, J=7.51 Hz, 3H).

Workup

  1. customwas sealed in a round bottom flask with a rubber septum
  2. customThe reaction mixture was purged with N2 gas
  3. customthe vessel was flushed with the H2 gas
  4. customthe complete consumption of the starting nitro compound so the reaction mixture
  5. filtrationwas filtered through celite
  6. customto remove the catalyst
  7. concentrationThe filtrate was concentrated onto silica gel
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e6ad717a92ac4204a9c0583762187957
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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