Potassium Iodide → Diphenylmethyl piperazinylbenzimidazole

HRID 2260102Notes

Reaction equation

HRID 2260102 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.[C:14]1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[C:27]1([CH:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:21]2[CH2:22][CH2:23][N:24]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[N:7]=[CH:6]3)[CH2:25][CH2:26]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 70048BenzhydrylpiperazineHCID 131055171-(3-Chloropropyl)-1H-benzimidazole

Product 1

HCID 13105518Diphenylmethyl piperazinylbenzimidazoleYield 18.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.5 g of 1-(3-chloropropyl)-1H-benzimidazole, 5.1 g of 1-(diphenylmethyl)piperazine, 3.7 g of sodium carbonate, 0.1 g of potassium iodide and 100 ml of 4-methyl-2-pentanone was stirred overnight at reflux temperature. After cooling, there was added water and the reaction mixture was separated. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.5 g (14.5%) of 1-[3-[4-(diphenylmethyl)-1-piperazinyl]propyl]-1H-benzimidazole; mp. 132.3° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customthe reaction mixture was separated
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 95:5)
  8. customThe eluent of the desired fraction was evaporated
  9. customthe residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-e9615ac299cd40b1b92123def2f0bf9a
Source dataset
uspto-grants-1995_12
Patent number
US05476853

Reaction notes

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