Potassium Iodide → HCID 21500240, compound

HRID 1729822Notes

Reaction equation

HRID 1729822 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1.[Cl:22][C:23]1[CH:38]=[CH:37][C:26]2[N:27]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:28](=[O:30])[NH:29][C:25]=2[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[OH2:30].[Cl:22][C:23]1[CH:38]=[CH:37][C:26]2[N:27]([CH:31]3[CH2:32][CH2:33][N:34]([CH2:2][CH2:3][CH2:4][CH:5]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:6]4[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:14])([F:15])[F:13])[CH:7]=4)[CH2:35][CH2:36]3)[C:28](=[O:30])[NH:29][C:25]=2[CH:24]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 21500281HCID 21500281, compound

Product 1

HCID 21500240HCID 21500240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 9.35 parts of 1-chloro-4-phenyl-4-(3-trifluoromethylphenyl)butane, 6.3 parts of 5-chloro-1-(4-piperidyl)-2-benzimidazolinone, 6.35 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. After cooling to room temperature, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The oily 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 residue is crystallized from 4-methyl-2-pentanone, yielding 5-chloro-1,3-dihydro-1-[1-{4-phenyl-4-[3-(trifluoromethyl)phenyl]butyl}4-piperidinyl]-2H-benzimidazol-2-one hydrate; mp. 114.9° C.

Workup

  1. customthe layers are separated
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe oily residue is purified by column-chromatography over silicagel
  6. additiona mixture of trichloromethane and 5% of methanol as eluent
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated
  9. customThe residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-a749190e73624e179354a6af1cd0beac
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

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