Potassium Iodide → HCID 23329047, compound

HRID 225136Notes

Reaction equation

HRID 225136 reaction equation
Cl[CH:2]([F:14])[CH2:3][CH:4]([OH:13])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].C(=O)([O-])O.[Na+].[C:20]1([N:26]2[C:30]3([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:29](=[O:36])[NH:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[I-].[K+]>C1(C)C=CC=CC=1>[O:36]=[C:29]1[C:30]2([CH2:31][CH2:32][N:33]([CH:2]([F:14])[CH2:3][CH:4]([OH:13])[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:6])[CH2:34][CH2:35]2)[N:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27][NH:28]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 516892Sodium BicarbonateHCID 19870779HCID 19870779, compound

Product 1

HCID 23329047HCID 23329047, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 18.75 g of γ-chloro-2-hydroxy-4-fluorobutyrophenone, 5.25 g of sodium hydrogen carbonate, 15 g of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 0.02 g of potassium iodide and 2 liters of toluene was refluxed for 80 hours. The resulting mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residual solid was washed with diethyl ether to give γ-(4-oxo-1-phenyl-1,3,8-triazaspiro[4,5]decan-8-yl)-2-hydroxy-4-fluorobutyrophenone, M.P. 215°-220° C.

Workup

  1. temperaturewas refluxed for 80 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. washThe residual solid was washed with diethyl ether

Sources & evidence

ORD record
ord-c04071ccb12b4e4eb9a949d80bbfd415
Source dataset
uspto-grants-1980_11
Patent number
US04235914

Reaction notes

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