Potassium Iodide → HCID 19038248, compound

HRID 263461Notes

Reaction equation

HRID 263461 reaction equation
[Cl:1]CCCO[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:18])[C:15]=1[CH2:16][OH:17])=[CH:12][CH:11]=[CH:10][CH:9]=2.[F:19][C:20]1[CH:33]=[CH:32][C:23]([C:24]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])=[CH:22][CH:21]=1.[C:34](=[O:37])([O-])[O-].[K+].[K+].[I-].[K+].[C:42](#N)[CH3:43]>>[ClH:1].[OH:17][CH2:16][C:15]1[C:14](=[O:18])[C:13]2[C:8](=[CH:9][C:10]([O:37][CH2:34][CH2:42][CH2:43][N:29]3[CH2:30][CH2:31][CH:26]([C:24](=[O:25])[C:23]4[CH:22]=[CH:21][C:20]([F:19])=[CH:33][CH:32]=4)[CH2:27][CH2:28]3)=[CH:11][CH:12]=2)[O:7][CH:6]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 131720061HCID 131720061, compound

Product 1

HCID 19038248HCID 19038248, compoundYield 18%

Procedure

A mixture of 1.6 g (6 mmole) of 7-(3-chloropropoxy-3-(hydroxymethyl)chromen-4-one, 1.2 g (6 mmole) de 4-(p-fluorobenzoyl)piperidine, 2 g (14 mmole) of anhydrous potassium carbonate and 0.5 g of potassium iodide in 30 ml of acetonitrile was heated for 24 hours at reflux, allowed to cool, filtered, and the filtrate was evaporated to dryness. The residue was dissolved in dichloromethane, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and evaporated. The product was dissolved in acetone and precipitated by addition of a hydrogen chloride solution. The precipitate was collected by filtration, washed with acetone, and recrystallized from methanol-ethyl ether to give 0.5 g (18%) of a solid, melting point 217°-218° C. (d).

Workup

  1. temperaturewas heated for 24 hours
  2. temperatureat reflux
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated
  10. dissolutionThe product was dissolved in acetone
  11. customprecipitated by addition of a hydrogen chloride solution
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with acetone
  14. customrecrystallized from methanol-ethyl ether

Sources & evidence

ORD record
ord-9951f229c4a044b8b7f3b59d549e5740
Source dataset
uspto-grants-1997_07
Patent number
US05643927

Reaction notes

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