Potassium Carbonate → HCID 19814311, compound

HRID 654444Notes

Reaction equation

HRID 654444 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:9][CH2:10]Br)=[CH:4][CH:3]=1.[OH:19][C:20]1([CH3:34])[C:24]2([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[O:23][C:22](=[O:30])[N:21]1[CH2:31][CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:9][CH2:10][N:27]2[CH2:28][CH2:29][C:24]3([O:23][C:22](=[O:30])[N:21]([CH2:31][CH2:32][CH3:33])[C:20]3([OH:19])[CH3:34])[CH2:25][CH2:26]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19814267HCID 19814267, compoundHCID 19814356HCID 19814356, compound

Product 1

HCID 19814311HCID 19814311, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

9.3 g of 3,3-bis(4-fluorophenyl)-2-propenyl bromide dissolved in 50 ml of acetone are portionwise added to a mixture containing 6.85 g of 4-hydroxy-4-methyl-2-oxo-3-n-propyl-1-oxa-3,8-diazaspiro[4,5]decane and 4.2 g of anhydrous potassium carbonate in 68 ml of anhydrous acetone at room temperature during 1 hour while stirring, then the reaction mixture is stirred at room temperature for an additional 1 hour. After filtering off the inorganic salts and evaporating the solvent under reduced pressure, the residue is taken up in benzene, washed with water, dried over anhydrous sodium sulfate and then the solution is evaporated to one tenth its volume under reduced pressure. The product is precipitated by adding n-hexane to the evaporation residue. The crystals are filtered off and dried to give the title compound in 86% yield, m.p.: 128°-129° C.

Workup

  1. additionare portionwise added to a mixture
  2. stirringthe reaction mixture is stirred at room temperature for an additional 1 hour
  3. filtrationAfter filtering off the inorganic salts
  4. customevaporating the solvent under reduced pressure
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solution is evaporated to one tenth its volume under reduced pressure
  8. customThe product is precipitated
  9. additionby adding n-hexane to the evaporation residue
  10. filtrationThe crystals are filtered off
  11. customdried

Sources & evidence

ORD record
ord-4b04a1f42f5540249e5b0d17082b1aa3
Source dataset
uspto-grants-1992_07
Patent number
US05132309

Reaction notes

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