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

HRID 1057306Notes

Reaction equation

HRID 1057306 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 98673341-{5-[5-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazineYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent

Procedure

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 (g) 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). MS m/z 430 (M++1).

Workup

  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)

Sources & evidence

ORD record
ord-399eb1c36c524d989b960226182eb424
Source dataset
uspto-grants-2003_02
Patent number
US06514966B2

Reaction notes

Loading…