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

HRID 276772

Reaction equation

HRID 276772 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[N:12]=2)=[CH:4][N:3]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CS(C)=O.[Cl-].[Na+].O>[Cl:20][C:15]1[CH:14]=[C:13]([C:11]2[N:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[N:3][CH:4]=3)[NH:9][CH:10]=2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 178477975HCID 178477975, compound

Product 1

HCID 178477952{5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazineYield 58.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2-Chloro-5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridine (72.8 g) and piperazine (61.8 g) in DMSO (478 mL) was heated to 105 degrees 16 hours. The reaction mixture was cooled to room temperature and diluted with 2500 mL half-saturated brine. The resultant precipitate was collected by filtration and triturated with 2000 mL hot methanol. The solids were collected by filtration, the mother liquor was concentrated to about 100 mL, and the additional precipitate was collected and combined with the original solids to provide 1-{5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine (49 g).

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. customtriturated with 2000 mL hot methanol
  3. filtrationThe solids were collected by filtration
  4. concentrationthe mother liquor was concentrated to about 100 mL
  5. customthe additional precipitate was collected

Sources & evidence

ORD record
ord-4fafef1542514aaaa5e91a3b425443f3
Source dataset
uspto-grants-2002_03
Patent number
US06355635B1

Linked notes

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