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

HRID 1014344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014344
[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>[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

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 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. NiCl2-6H2O (0.247 g, 1.04 mmol) was added, followed by slow addition of NaBH4 (0.392 g, 10.38 mmol). The reaction mixture was adsorbed on SiO2 and purified via column chromatography to afford 2-(methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline. (0.925 g, 3.24 mmol, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.91 (s, 3 H) 2.99-3.07 (m, 4 H) 3.19-3.27 (m, 4 H) 3.75 (s, 3 H) 4.28 (s, 2 H) 6.33 (dd, J=8.39, 2.43 Hz, 1 H) 6.49-6.58 (m, 2 H). ESIMS M+H)+=285.

Aufarbeitung

  1. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0d39f6e85ff841e68ea5e7f37a57c34f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981903B2

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