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 419595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419595
[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]

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-73bf14737d9f41b18cafdf3c2d8880f2
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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