Sodium borohydride → 5-Methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline

HRID 419649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419649
[BH4-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([O:13][CH3:14])=[CH:6][C:5]=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>C1COCC1.CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:3][C:4]1[C:5]([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:6][C:7]([O:13][CH3:14])=[C:8]([CH:9]=1)[NH2:10]

Komponenten

6

Edukt 2

HCID 4311764Sodium borohydrideHCID 594529721-{1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine

Produkt 1

HCID 594526035-Methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}anilineAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11791229Dichloronickel;hexahydrateKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.30 g, 7.93 mmol) was added in portions to a stirring suspension of 1-{1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine (1.09 g, 2.64 mmol) and Nickel(II)chloride hexahydrate (0.19 g, 0.8 mmol) in THF (10 mL) and MeOH (20 mL) at rt. The reaction mixture was allowed to stir at rt for 2 h and then it was concentrated in vacuo. The residue was taken up in DCM and passed through a bed of celite. The resultant filtrate was then concentrated onto silica gel and purified by flash chromatography to afford 5-methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (0.58 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.55 (s, 1H), 6.43 (s, 1H), 4.30 (s, 2H), 3.70 (s, 3H), 3.05-3.15 (m, 4H), 2.89-2.96 (m, 2H), 2.86 (s, 3H), 2.52-2.65 (m, 6H), 2.26-2.41 (m, 1H), 2.06 (s, 3H), 1.74-1.85 (m, 2H), 1.43-1.63 (m, 2H).

Aufarbeitung

  1. concentrationit was concentrated in vacuo
  2. concentrationThe resultant filtrate was then concentrated onto silica gel
  3. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-953b4dc7bc28437b8abaf331e947f3cf
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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