Potassium Iodide → HCID 21500287, compound

HRID 1729823Notes

Reaction equation

HRID 1729823 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[Cl:20][C:21]1[CH:37]=[CH:36][C:24]2[N:25]([CH:29]3[CH2:34][CH2:33][NH:32][CH:31]([CH3:35])[CH2:30]3)[C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[Cl:20][C:21]1[CH:37]=[CH:36][C:24]2[N:25]([CH:29]3[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][CH:5]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)[C:6]4[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=4)[CH:31]([CH3:35])[CH2:30]3)[C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 21500246HCID 21500246, compound

Product 1

HCID 21500287HCID 21500287, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 7 parts of 1-chloro-4,4-bis(4-fluorophenyl)-butane, 5.5 parts of 5-chloro-1,3-dihydro-1-(2-methyl-4-piperidinyl)-2H-benzimidazol-2-one, 6.4 parts of sodium carbonate, 0.2 parts of potassium iodide and 160 parts of 4-methyl-2-pentanone is stirred and refluxed for 36 hours. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The oily residue is converted into the hydrochloride salt in 2-propanol and 2,2'-oxybispropane. The salt is filtered off. The free base is liberated in the conventional manner and extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silicagel, using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is crystallized from 2-propanol, yielding 5-chloro-1-{1-[4,4-bis(4-fluorophenyl)butyl]- 2-methyl-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 171.1° C.

Workup

  1. temperaturerefluxed for 36 hours
  2. temperatureAfter cooling
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt is filtered off
  8. extractionextracted with methylbenzene
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is purified by column-chromatography over silicagel
  13. additiona mixture of trichloromethane and 5% of methanol as eluent
  14. customThe pure fractions are collected
  15. customthe eluent is evaporated
  16. customThe oily residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-e9ccc8ac52464cd2805638f87ac92bae
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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