Potassium Iodide → HCID 54155158, compound

HRID 258859Notes

Reaction equation

HRID 258859 reaction equation
Cl[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].Cl.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([CH:26]2[CH2:31][CH2:30][N:29]([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][CH2:27]2)=[O:25])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 133608891-(4-chlorobutyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 54155158HCID 54155158, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4 parts of 1-(4-chlorobutyl)-1,3-dihydro-2H-benzimidazol-2-one, 4 parts of (4-fluorophenyl) (4-piperidinyl) methanone hydrochloride, 10 parts of sodium carbonate, 0.2 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The solid residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 10% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 2 parts (30%) of 1-{4-[4-(4-fluorobenzoyl)-1-piperidinyl]butyl} -1,3-dihydro-2H-benzimidazol-2-one; mp. 176.5° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 10% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-fc9d249e84de44eebf843f8c59c1d2ba
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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