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

HRID 2050300Notes

Reaction equation

HRID 2050300 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15].[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[ClH:1].[ClH:1].[F:36][C:33]1[CH:32]=[CH:31][C:30]([CH:23]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[N:24]2[CH2:25][CH2:26][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[NH:8][C:7]3=[O:15])[CH2:28][CH2:29]2)=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 133608891-(4-chlorobutyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 205062941-[4-{4-[bis(4-fluorophenyl)methyl]-1-piperazinyl}butyl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.94 parts of 1-(4-chlorobutyl)-1,3-dihydro-2H-benzimidazol-2-one, 5.76 parts of 1-[bis(4-fluorophenyl)methyl]piperazine, 5.3 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 20 hours with water-separator. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from ethanol. The product is filtered off and dried, yielding 1-[4-{4-[bis(4-fluorophenyl)methyl]-1-piperazinyl}butyl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride. hydrate. hemiethanolate; mp. 172.9° C.

Workup

  1. temperatureAfter cooling
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from ethanol
  7. filtrationThe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-f97ce1a1df92407592231264c8e5ea52
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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