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

HRID 419595Notes

Reaction equation

HRID 419595 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]([N:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1)[CH3:2]>CCOC(C)=O.[Pt]>[CH2:1]([C:3]1[C:4]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:22][CH2:23][N:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:25][CH2:26]3)[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

4

Reactant 1

HCID 594527591-{1-[2-Ethyl-5-(ethyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine

Product 1

HCID 594526865-Ethyl-2-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}anilineYield 95%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-{1-[2-ethyl-5-(ethyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine (0.511 g, 1.160 mmol) and sulfided platinum on carbon (0.181 g, 0.046 mmol) in EtOAc (30 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 48 h. TLC analysis showed the complete consumption of the starting nitro compound so the reaction vessel was purged with N2 and 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-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (0.452 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.58 (s, 1H), 6.47 (s, 1H), 4.33 (br. s., 2H), 3.94 (q, J=6.93 Hz, 2H), 3.04-3.15 (m, 4H), 2.79-2.93 (m, 5H), 2.54-2.66 (m, 6H), 2.28-2.40 (m, 1H), 1.72-1.85 (m, 2H), 1.45-1.61 (m, 2H), 1.30 (t, J=6.92 Hz, 3H), 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 vessel
  5. customwas purged with N2
  6. filtrationthe reaction mixture was filtered through celite
  7. customto remove the catalyst
  8. concentrationThe filtrate was concentrated onto silica gel
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-73bf14737d9f41b18cafdf3c2d8880f2
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…