Methanol → 1-(3-Aminophenyl)-4-methylpiperazin-2-one

HRID 1362862

Reaktionsgleichung

Reaktionsgleichung von HRID 1362862
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1.C[OH:18]>O.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][C:4]2=[O:18])[CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 887MethanolHCID 121521611-Methyl-4-(3-nitrophenyl)piperazine

Produkt 1

HCID 579741721-(3-Aminophenyl)-4-methylpiperazin-2-oneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Pd/C (10%, 420 mg) was added to a solution of 1-methyl-4-(3-nitrophenyl)piperazine (8.4 g) in methanol (500 mL) and water (20 mL). The reaction mixture was stirred and degassed with nitrogen, and the vessel was charged with H2 gas at atmospheric pressure. The reaction was allowed to proceed overnight after which time the Pd/C was removed by filtration over celite and the methanol and water were removed in vacuo to give 1-(3-aminophenyl)-4-methyl-2-piperazinone as a yellow solid (7.08 g, 95% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.07 (1H, t, J=7.83 Hz) 6.48-6.55 (2H, m) 6.46 (1H, d, J=1.01 Hz) 6.44 (1H, s) 3.88 (4H, s) 3.54 (2H, br. s.) 2.82 (3H, s)

Aufarbeitung

  1. customdegassed with nitrogen
  2. additionthe vessel was charged with H2 gas at atmospheric pressure
  3. customafter which time the Pd/C was removed by filtration over celite
  4. customthe methanol and water were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e6cbaab4cf6a459c9bc6204f9df511d5
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884098B2

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