Potassium Iodide → 1-[1-(4,4-Diphenylcyclohexyl)-4-piperidyl]-2-benzimidazolinone

HRID 616990Notes

Reaction equation

HRID 616990 reaction equation
S(C1C=CC(C)=CC=1)(O[CH:5]1[CH2:10][CH2:9][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=O)=O.[NH:30]1[CH2:35][CH2:34][CH:33]([N:36]2[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[NH:38][C:37]2=[O:45])[CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:11]1([C:8]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:7][CH2:6][CH:5]([N:30]3[CH2:31][CH2:32][CH:33]([N:36]4[C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=5[NH:38][C:37]4=[O:45])[CH2:34][CH2:35]3)[CH2:10][CH2:9]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 203669124,4-Diphenylcyclohexyl tosylate

Product 1

HCID 203668871-[1-(4,4-Diphenylcyclohexyl)-4-piperidyl]-2-benzimidazolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4.1 g of 4,4-diphenylcyclohexyl tosylate, 2.2 g of 4-piperidyl-2-benzimidazolinone, 1.5 g of potassium carbonate, 1.5 g of potassium iodide and 50 ml of dimethylformamide is stirred at 55° C for 47 hours. The reaction mixture is cooled to room temperature and poured into ice water. The precipitate is collected by filtration and dissolved in chloroform under warming. The solution is washed with water and dried over sodium sulfate, and the chloroform is removed under reduced pressure. To the residue is added ether, and the mixture is cooled. The precipitated crystals are collected by filtration and recrystallized twice from a mixture of methanol and chloroform. The crystals are dried at 100° C under reduced pressure for many hours, because the solvent is not easily removable. Thus is obtained 1-[1-(4,4-diphenylcyclohexyl)-4-piperidyl]-2-benzimidazolinone as light gray crystals, melting at 289°-293° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe precipitate is collected by filtration
  3. dissolutiondissolved in chloroform
  4. temperatureunder warming
  5. washThe solution is washed with water
  6. dry with materialdried over sodium sulfate
  7. customthe chloroform is removed under reduced pressure
  8. additionTo the residue is added ether
  9. temperaturethe mixture is cooled
  10. filtrationThe precipitated crystals are collected by filtration
  11. customrecrystallized twice from a mixture of methanol and chloroform
  12. customThe crystals are dried at 100° C under reduced pressure for many hours, because the solvent

Sources & evidence

ORD record
ord-491a0f48e31e40e090b3837a05713902
Source dataset
uspto-grants-1978_02
Patent number
US04076821

Reaction notes

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