Methanol → 2-(Methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline

HRID 419644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419644
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.CO.[BH4-].[Na+]>C1COCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydride2×HCID 598602551-(3-Methoxy-4-nitro-phenyl)-4-methylsulfonyl-piperazine

Produkt 1

HCID 598602722-(Methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11791229Dichloronickel;hexahydrateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-[3-(Methyloxy)-4-nitrophenyl]-4-(methylsulfonyl)piperazine (1.09 g, 3.46 mmol) was suspended in 5 mL THF and 10 mL MeOH in a 100 mL round bottom flask. Nickle(II)chloride hexahydrate (0.247 g, 1.04 mmol) was added followed by slow addition of NaBH4 (0.392 g, 10.38 mmol). TLC analysis indicated reaction complete after addition of NaBH4. Reaction mixture was adsorbed on SiO2 and purified via column chromatography using a gradient of 0-10% MeOH in DCM. Fractions were combined and rotovapped to give the title compound of step B. (0.925 g, 3.24 mmol, 93%); MS (ESI): 285 [M+H]+.

Aufarbeitung

  1. customreaction
  2. customReaction mixture
  3. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-93280bf8391f478da0bd341a2fbbe156
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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