Potassium Iodide → 8-[4,4-Bis(4-fluorophenyl)-3-butenyl]-4-methylene-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4,5]decane

HRID 466614Notes

Reaction equation

HRID 466614 reaction equation
[CH2:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[O:5][C:4](=[O:12])[N:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[CH:27][CH2:28][CH2:29]Cl)=[CH:22][CH:21]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)=[CH:27][CH2:28][CH2:29][N:9]2[CH2:10][CH2:11][C:6]3([O:5][C:4](=[O:12])[N:3]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:2]3=[CH2:1])[CH2:7][CH2:8]2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1023921,1'-(4-Chloro-1-butenylidene)bis[4-fluorobenzene]HCID 198142774-Methylene-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4,5]decane

Product 1

HCID 198142408-[4,4-Bis(4-fluorophenyl)-3-butenyl]-4-methylene-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4,5]decaneYield 83.5%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture containing 8.4 g of 4-methylene-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4,5]decane, 18.4 g of 4,4-bis(4-fluorophenyl)-3-butenyl chloride, 0.3 g of potassium iodide, 9.2 g of anhydrous potassium carbonate and 81 ml of methyl isobutyl ketone is mildly refluxed under argon while stirring for 12 hours. After cooling down and filtering off the inorganic salts, the precipitate is washed with methyl isobutyl ketone, the filtrate is washed with water to neutral, dried over anhydrous magnesium sulfate, then the solvent is evaporated under reduced pressure. After triturating the evaporation residue with n-hexane, the precipitate is filtered and recrystallized from ethanol to give the title compound in 83.5% yield, m.p.: 136.5°-137.5° C.

Workup

  1. temperatureis mildly refluxed under argon
  2. temperatureAfter cooling down
  3. filtrationfiltering off the inorganic salts
  4. washthe precipitate is washed with methyl isobutyl ketone
  5. washthe filtrate is washed with water to neutral,
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customAfter triturating the evaporation residue with n-hexane
  9. filtrationthe precipitate is filtered
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-55658fc1fb054cf38eeeaa6fa3f197da
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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