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 419628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419628
[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]

Komponenten

5

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4d7b5df09c0c4765873f1ddae3e27be4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

Notizen zur Reaktion

Wird geladen…