Potassium Iodide → 2H-Benzimidazol-2-one, 1,3-dihydro-1-(1-(4,4-bis(4-fluorophenyl)cyclohexyl)-4-piperidinyl)-5-chloro-

HRID 616992Notes

Reaction equation

HRID 616992 reaction equation
S(C1C=CC(C)=CC=1)(O[CH:5]1[CH2:10][CH2:9][C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=O)=O.[NH:32]1[CH2:37][CH2:36][CH:35]([N:38]2[C:42]3[CH:43]=[CH:44][C:45]([Cl:47])=[CH:46][C:41]=3[NH:40][C:39]2=[O:48])[CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CCOCC.O.CN(C)C=O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:7][CH2:6][CH:5]([N:32]3[CH2:33][CH2:34][CH:35]([N:38]4[C:42]5[CH:43]=[CH:44][C:45]([Cl:47])=[CH:46][C:41]=5[NH:40][C:39]4=[O:48])[CH2:36][CH2:37]3)[CH2:10][CH2:9]2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 20366914HCID 20366914, compound

Product 1

HCID 30459002H-Benzimidazol-2-one, 1,3-dihydro-1-(1-(4,4-bis(4-fluorophenyl)cyclohexyl)-4-piperidinyl)-5-chloro-

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 11 g of 4,4-bis(p-fluorophenyl)cyclohexyl tosylate, 6 g of 1-(4-piperidyl)-5-chloro-2-benzimidazolinone, 3.5 g of potassium carbonate, 4.1 g of potassium iodide and 80 ml of dimethylformamide is stirred at 70°-80° C for 64 hours. The reaction mixture is poured into water, ether is added to the separated semi-solid, and the whole is stirred for 30 minutes. The substance insoluble in water and ether is collected by filtration, washed with ether and dried. The obtained crystals are dissolved in a mixture of chloroform and methanol (9:1), and the solution is concentrated to some degree and cooled. The precipitated crystals are collected by filtration and purified in the same manner to give 1-[1-(4,4-bis(p-fluorophenyl)cyclohexyl)-4-piperidyl]-5-chloro-2-benzimidazolinone as white crystals, melting at 279°-284° C.

Workup

  1. additionis added to the separated semi-solid
  2. stirringthe whole is stirred for 30 minutes
  3. filtrationThe substance insoluble in water and ether is collected by filtration
  4. washwashed with ether
  5. customdried
  6. dissolutionThe obtained crystals are dissolved in a mixture of chloroform and methanol (9:1)
  7. concentrationthe solution is concentrated to some degree
  8. temperaturecooled
  9. filtrationThe precipitated crystals are collected by filtration
  10. custompurified in the same manner

Sources & evidence

ORD record
ord-30367c1dca2c45798308895eb59e9ad0
Source dataset
uspto-grants-1978_02
Patent number
US04076821

Reaction notes

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