1-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine → 4-(4-Isopropylpiperazin-1-YL)-2-methoxyphenylamine

HRID 419550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419550
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:6][CH2:5]1)[CH3:3]>CCO>[CH3:3][CH:2]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:8][CH2:9]1)[CH3:1]

Komponenten

3

Edukt 1

HCID 587484431-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine

Produkt 1

HCID 457907394-(4-Isopropylpiperazin-1-YL)-2-methoxyphenylamineAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In a pressure vessel was placed a solution of 1-(1-methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine (4.0 g, 14.3 mmol) in EtOH (100 mL). The solution was purged with N2 for 15 min before the addition of 10% Pd/carbon (0.5 g). The reaction was stirred at rt for 5 h under 60 psi H2. After releasing H2 pressure, filtration removed the solid resin, and the filtrate was concentrated and purified with silica gel chromatography to furnish the title compound of step B (3.6 g, 99% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.09 (d, J=6.6 Hz, 6H), 2.66-2.75 (m, 5H), 3.05-3.10 (m, 4H), 3.47 (s, 3H), 3.83 (s, 2H), 6.42 (dd, J=8.2, 2.4 Hz, 1H), 6.52 (d, J=2.2 Hz, 1H), 6.64 (d, J=8.4 Hz, 1H).

Aufarbeitung

  1. customIn a pressure vessel was placed
  2. customThe solution was purged with N2 for 15 min before the addition of 10% Pd/carbon (0.5 g)
  3. filtrationH2 pressure, filtration
  4. customremoved the solid resin
  5. concentrationthe filtrate was concentrated
  6. custompurified with silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-faa4054825184d9fb7ccc551902d10d6
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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