Potassium Iodide → 1-{5-[5-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazine

HRID 276773

Reaktionsgleichung

Reaktionsgleichung von HRID 276773
Cl.Cl.Cl[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)=[CH:6][N:5]=1.[CH2:23]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH:24]([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C1CCCCC1>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[NH:14][C:10]([C:7]3[CH:8]=[CH:9][C:4]([N:30]4[CH2:31][CH2:32][N:27]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:28][CH2:29]4)=[N:5][CH:6]=3)=[N:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium Carbonate2×HCID 20520521-(2-Methylpropyl)piperazineHCID 1784785732-chloro-5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridine dihydrochloride

Produkt 1

HCID 98673341-{5-[5-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazineAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

A suspension of 2-chloro-5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridine dihydrochloride (1.07 g, 2.6 mmol), N-isobutylpiperazine (0.95 g, 6.72 mmol), potassium carbonate (0.5 g, 3.62 mmol), and potassium iodide (0.5 g, 0.54 mmol) in xylenes (5 mL) was heated to reflux under a nitrogen atmosphere for 24 hours. The reaction mixture was then cooled to ambient temperature and a solution of potassium carbonate (19) in water (10 mL) and cyclohexane (10 mL) were added. The mixture was stirred vigorously for 15 min, and the precipitate was collected by filtration. The filter cake was washed with water (10 mL) and triturated with methyl tert-butyl ether (4 mL) to provide 1-{5-[5(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazine (2.07 mmol).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under a nitrogen atmosphere for 24 hours
  3. filtrationthe precipitate was collected by filtration
  4. washThe filter cake was washed with water (10 mL)
  5. customtriturated with methyl tert-butyl ether (4 mL)

Quellen und Nachweise

ORD-Eintrag
ord-f5a3b30afdc447b988dd4d805b8e252d
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355635B1

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