Potassium Iodide → HCID 13364155, compound

HRID 616997Notes

Reaction equation

HRID 616997 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.[Cl:32][C:33]1[CH:34]=[C:35]([N:40]2[C:44]3([CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)[C:43](=[O:50])[NH:42][CH2:41]2)[CH:36]=[CH:37][C:38]=1[F:39].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>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:47]3[CH2:46][CH2:45][C:44]4([N:40]([C:35]5[CH:36]=[CH:37][C:38]([F:39])=[C:33]([Cl:32])[CH:34]=5)[CH2:41][NH:42][C:43]4=[O:50])[CH2:49][CH2:48]3)[CH2:10][CH2:9]2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 133641461-(3-Chloro-4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-oneHCID 20366914HCID 20366914, compound

Product 1

HCID 13364155HCID 13364155, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.6 g of 4,4-bis(p-fluorophenyl)cyclohexyl tosylate, 5.7 g of 1-(3-chloro-4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one (m.p. 194.5°-196.5° C), 3.3 g of potassium carbonate, 4 g of potassium iodide and 50 ml of dimethylformamide is stirred at 75°-80° C for 5 hours. The reaction mixture is poured into water, and the precipitated crystals are collected by filtration, dried in a desiccator and dissolved in a mixture of chloroform and methanol (9:1). The solution is concentrated to some degree and cooled. The precipitated crystals are collected by filtration and purified in the same manner to give 8-[4,4-bis(p-fluorophenyl)cyclohexyl]-1-(3-chloro-4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one as white crystals, melting at 201°-203° C.

Workup

  1. filtrationthe precipitated crystals are collected by filtration
  2. customdried in a desiccator
  3. dissolutiondissolved in a mixture of chloroform and methanol (9:1)
  4. concentrationThe solution is concentrated to some degree
  5. temperaturecooled
  6. filtrationThe precipitated crystals are collected by filtration
  7. custompurified in the same manner

Sources & evidence

ORD record
ord-5ffd6924c93747c9b5ecce2fd593256e
Source dataset
uspto-grants-1978_02
Patent number
US04076821

Reaction notes

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