1-{[4-(2-Methoxy-5-nitrophenyl)furan-2-yl]methyl}-4-methylpiperazine → (4-Methoxy-3-[5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amine

HRID 1593790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593790
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]1[CH:13]=[C:14]([CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[O:15][CH:16]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:12]1[CH:13]=[C:14]([CH2:17][N:18]2[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]2)[O:15][CH:16]=1

Komponenten

5

Edukt 2

HCID 160991751-{[4-(2-Methoxy-5-nitrophenyl)furan-2-yl]methyl}-4-methylpiperazineHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 16099182(4-Methoxy-3-[5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-{[4-(2-methoxy-5-nitrophenyl)-2-furyl]methyl}-4-methylpiperazine (396 mg, 1.19 mmol) in 20 mL of methanol was added 10% palladium on carbon (40 mg). The resulting mixture was shaken with hydrogen in a Parr shaker until hydrogen uptake ceased. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give 358 mg (100%) of (4-methoxy-3-[5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amine as a brown oil, 1H NMR (DMSO-d6) δ 2.14 (s, 3H), 2.29 (broad s, 4H), 2.40 (broad s, 4H), 3.49 (s, 2H), 3.72 (s, 3H), 4.61 (s, 2H), 6.47 (d, J=8 Hz, 1H), 6.58 (s, 1H), 6.78 (d, J=9 Hz, 1H), 6.80 (s, 1H), 7.91 (s, 1H); MS 302.1 (M+H)+.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-afdccee143b94d8aa032de058271421b
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297795B2

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