Water → HCID 59454338, Verbindung

HRID 1914754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914754
[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)[C:9]=2[C:17](=[O:19])[CH3:18])[CH2:4][CH2:3]1.C1CCCCC=1.C1COCC1.O>Cl.[Pd].CCO>[NH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[C:9]=1[C:17](=[O:19])[CH3:18]

Komponenten

8

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8079CyclohexeneHCID 594543161-[2-(4-Methyl-1-piperazinyl)-6-nitrophenyl]ethanone

Produkt 1

HCID 59454338HCID 59454338, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 1-[2-(4-methyl-piperazin-1-yl)-6-nitro-phenyl]-ethanone (270 mg, 1.02 mmol) in a mixture (1:1:1.5:2.5) of cyclohexene:THF:H2O:EtOH (12 ml), Pd/C 10% (328 mg) and two drops of HCl 37% were added. The mixture was heated at 70° C. for 3 hours. The Pd was filtered from the reaction and the solvents were removed from the filtrate under reduced pressure. The crude was purified by flash chromatography (DCM/MeOH/7N NH3 in methanol 9:1:1), to give the final compound (225 mg, 95% yield) as orange oil. This was treated with HCl in dioxane, in order to obtain a more manageable solid.

Aufarbeitung

  1. filtrationThe Pd was filtered from the reaction
  2. customthe solvents were removed from the filtrate under reduced pressure
  3. customThe crude was purified by flash chromatography (DCM/MeOH/7N NH3 in methanol 9:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ae06d0dca36d475ca2fc3053e0203e62
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614220B2

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