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

HRID 654449Notes

Reaction equation

HRID 654449 reaction equation
[CH2:1]([N:3]1[C:7](=[CH2:8])[C:6]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[O:5][C:4]1=[O:14])[CH3:2].C(N(CC)CC)C.[I-].[K+].[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)=[CH:32][CH2:33][CH2:34]Cl)=[CH:27][CH:26]=1>C(C(C)=O)C>[F:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]([C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)=[CH:32][CH2:33][CH2:34][N:11]2[CH2:12][CH2:13][C:6]3([O:5][C:4](=[O:14])[N:3]([CH2:1][CH3:2])[C:7]3=[CH2:8])[CH2:9][CH2:10]2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 1023921,1'-(4-Chloro-1-butenylidene)bis[4-fluorobenzene]HCID 198142543-Ethyl-4-methylene-2-oxo-1-oxa-3,8-diazaspiro[4,5]decane

Product 1

HCID 198143138-[4,4-Bis(4-fluorophenyl)-3-butenyl]-3-ethyl-4-methylene-2-oxo-1-oxa-3,8-diazaspiro[4,5]decaneYield 68.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture containing 7.8 g of 3-ethyl-4-methylene-2-oxo-1-oxa-3,8-diazaspiro[4,5]decane, 8.5 ml of anhydrous triethylamine, 80 ml of anhydrous methyl ethyl ketone, 0.3 g of potassium iodide and 16.7 g of 4,4-bis(4-fluorophenyl)-3-butenyl chloride is refluxed under nitrogen while stirring for 15 hours, then the solvent is distilled off under reduced pressure. After adding benzene and water to the residue, the benzene layer is washed with water to neutral, dried over anhydrous magnesium sulfate, filtered through an aluminum oxide bed and evaporated under reduced pressure. After recrystallizing the residue from ethanol, the title product is obtained in 68.7% yield, m.p.: 138°-139° C.

Workup

  1. temperatureis refluxed under nitrogen
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionAfter adding benzene and water to the residue
  4. washthe benzene layer is washed with water to neutral,
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered through an aluminum oxide bed
  7. customevaporated under reduced pressure
  8. customAfter recrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-f832168ce77745aea9a1bf2969230872
Source dataset
uspto-grants-1992_07
Patent number
US05132303

Reaction notes

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