cis-3,5-Dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine → 5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

HRID 130400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130400
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([N+:17]([O-])=O)[CH:10]=2)[CH2:3]1>C(O)C.[Pd]>[CH3:8][C@H:6]1[NH:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:10]=2)[NH2:17])[CH2:5]1

Komponenten

4

Edukt 1

HCID 59007052cis-3,5-Dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine

Produkt 1

HCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of cis-3,5-dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine (D3) (2.65 g, 10 mmol) in ethanol (60 ml) containing palladium on charcoal (300 mg, 10% paste) was stirred under aone atmosphere of hydrogen gas overnight. The mixture was filtered through celite, the pad washed in ethanol and the combined ethanol solutions evaporated. The residue was purified by column chromatography (Biotage (SiO2) 100 g, dichloromethane to 1:10 2M ammonia in methanol:dichloromethane) to afford the title product (D4). MS (ES+) m/e 236 [M+H]+.

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. washthe pad washed in ethanol
  3. customthe combined ethanol solutions evaporated
  4. customThe residue was purified by column chromatography (Biotage (SiO2) 100 g, dichloromethane to 1:10 2M ammonia in methanol:dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-02667bc13b9349a1a9663f31c9975be8
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381728B2

Notizen zur Reaktion

Wird geladen…