Potassium Iodide → 1-[6-{4-[bis(4-fluorophenyl)methyl]-1-piperazinyl}hexyl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride

HRID 354988Notes

Reaction equation

HRID 354988 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10](C(C)=C)[C:9]1=[O:20].[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[ClH:1].[ClH:1].[F:41][C:38]1[CH:37]=[CH:36][C:35]([CH:28]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)[N:29]2[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[NH:10][C:9]3=[O:20])[CH2:33][CH2:34]2)=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 205063391-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

Product 1

HCID 205062961-[6-{4-[bis(4-fluorophenyl)methyl]-1-piperazinyl}hexyl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.65 parts of 1-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 2.9 parts of 1-[bis(4-fluorophenyl)methyl]piperazine, 2.65 parts of sodium carbonate, 0.1 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol. The solvent is evaporated and the residue is dissolved in water. The free base is liberated in the conventional manner with ammonium hydroxide and extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in ethanol and 2-propanol. The salt is filtered off and dried, yielding 1-[6-{4-[bis(4-fluorophenyl)methyl]-1-piperazinyl}hexyl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride; mp. 204.5° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol
  8. customThe solvent is evaporated
  9. dissolutionthe residue is dissolved in water
  10. extractionextracted with trichloromethane
  11. customThe extract is dried
  12. filtrationfiltered
  13. customevaporated
  14. filtrationThe salt is filtered off
  15. customdried

Sources & evidence

ORD record
ord-8cb58884f47f437b989de398075743ff
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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