1-Methyl-4-(4-methyl-3-nitrophenyl)piperazine → 2-Methyl-5-(4-methylpiperazin-1-yl)benzenamine

HRID 1907441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907441
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1>C(O)C.C1CCCCC=1.[Pd]>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:9][C:10]=1[NH2:15]

Komponenten

5

Edukt 1

HCID 581716321-Methyl-4-(4-methyl-3-nitrophenyl)piperazine

Produkt 1

HCID 249941402-Methyl-5-(4-methylpiperazin-1-yl)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8079CyclohexeneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-methyl-4-(4-methyl-3-nitro-phenyl)-piperazine (9.0 g, 38.29 mmol) in ethanol (100 mL) and cyclohexene (7 ml), Pd/C 10% (1.5 g) was added. The mixture was heated at 80° C. for 6 hours until HPLC revealed the disappearance of the starting material. The Pd was filtered from the reaction and the solvents were removed from the filtrate under reduced pressure. The crude was diluted with DCM and treated with HCl in dioxane; the precipitate was collected and washed with diethyl ether to give the final compound as a brown solid in quantitative yield.

Aufarbeitung

  1. filtrationThe Pd was filtered from the reaction
  2. customthe solvents were removed from the filtrate under reduced pressure
  3. additionThe crude was diluted with DCM
  4. additiontreated with HCl in dioxane
  5. customthe precipitate was collected
  6. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8ae15f576e02456c82c4b28391496808
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598172B2

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