Potassium Iodide → HCID 13078373, compound

HRID 223252Notes

Reaction equation

HRID 223252 reaction equation
Br.[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][N:9]=[C:8]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:7]=2[CH:17]=1.C(=O)(O)[O-].[Na+].[I-].[K+].[Cl:25][CH2:26][CH2:27][CH2:28][CH:29]([C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1>O.CN(C)C=O>[ClH:25].[F:36][C:33]1[CH:32]=[CH:31][C:30]([CH:29]([C:37]2[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=2)[CH2:28][CH2:27][CH2:26][N:14]2[CH2:13][CH2:12][CH:11]([C:8]3[C:7]4[CH:17]=[C:3]([OH:2])[CH:4]=[CH:5][C:6]=4[O:10][N:9]=3)[CH2:16][CH2:15]2)=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 516892Sodium BicarbonateHCID 13076434HCID 13076434, compound

Product 1

HCID 13078373HCID 13078373, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g of 5-hydroxy-3-(4-piperidyl)-1,2-benzisoxazole hydrobromide, 0.84 g of sodium bicarbonate, 25 ml of dimethylformamide, a few crystals of potassium iodide and 1.4 g of 4-chloro-1,1-bis(4-fluorophenyl)butane was stirred at 90° for 8 hrs. After cooling to ambient temperature, the mixture was poured into water and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed with water and brine, and the the solvent was removed in vacuo to yield a solid. The solid was triturated with ether and was filtered. The filter cake was partially dissolved in ethanol and a saturated methanol-hydrogen chloride solution was added, followed by warming to obtain a solution. The salt was precipitated by adding ether. Two recrystallizations from ethanol-ether afforded 1.0 g (40%) of product, mp 234°-236°.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate
  2. washThe ethyl acetate was washed with water and brine
  3. customthe the solvent was removed in vacuo
  4. customto yield a solid
  5. customThe solid was triturated with ether
  6. filtrationwas filtered
  7. dissolutionThe filter cake was partially dissolved in ethanol
  8. additiona saturated methanol-hydrogen chloride solution was added
  9. temperatureby warming
  10. customto obtain a solution
  11. customThe salt was precipitated
  12. additionby adding ether
  13. customTwo recrystallizations from ethanol-ether

Sources & evidence

ORD record
ord-465987cc748846a88d3182a4639b9c54
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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