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Potassium Iodide → 8-[4,4-Bis(p-fluorophenyl)cyclohexyl]-1-(p-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one

HRID 616996
Notes
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Reaction equation

HRID 616996 reaction equation
S(O[CH:6]1[CH2:11][CH2:10][C:9]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=O)(=O)C.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:37]3([CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[C:36](=[O:43])[NH:35][CH2:34]2)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(OC(C)C)(C)C>O.CN(C)C=O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:9]2([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)[CH2:8][CH2:7][CH:6]([N:40]3[CH2:39][CH2:38][C:37]4([N:33]([C:30]5[CH:29]=[CH:28][C:27]([F:26])=[CH:32][CH:31]=5)[CH2:34][NH:35][C:36]4=[O:43])[CH2:42][CH2:41]3)[CH2:11][CH2:10]2)=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 939151-(4-Fluorophenyl)-1,3,8-triazaspiro(4.5)decan-4-oneHCID 203668854,4-Bis(p-fluorophenyl)cyclohexyl mesylate

Product 1

HCID 13364151
8-[4,4-Bis(p-fluorophenyl)cyclohexyl]-1-(p-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 16 g of 4,4-bis(p-fluorophenyl)cyclohexyl mesylate, 10 g of 1-(p-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one (m.p. 234°-234.5° C), 6.1 g of potassium carbonate, 7.3 g of potassium iodide and 100 ml of dimethylformamide is stirred at 70°-80° C for 50 hours. The reaction mixture is poured into water, isopropyl ether is added to the aqueous mixture, and the resulting mixture is stirred for some time. The precipitated crystals are collected by filtration and dissolved in a mixture of chloroform and methanol (9:1). The solvent is removed to some degree and cooled in an ice bath. The precipitated crystals are collected by filtration and purified in the same manner to give 8-[4,4-bis(p-fluorophenyl)cyclohexyl]-1-(p-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one as white crystals, melting at 237°-240° C.

Workup

  1. additionis added to the aqueous mixture
  2. stirringthe resulting mixture is stirred for some time
  3. filtrationThe precipitated crystals are collected by filtration
  4. dissolutiondissolved in a mixture of chloroform and methanol (9:1)
  5. customThe solvent is removed to some degree
  6. temperaturecooled in an ice bath
  7. filtrationThe precipitated crystals are collected by filtration
  8. custompurified in the same manner

Sources & evidence

ORD record
ord-ff2233a8833a477bb5ba29a4969d5d31
Source dataset
uspto-grants-1978_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04076821

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes