Potassium Iodide → HCID 13319850, compound

HRID 745316Notes

Reaction equation

HRID 745316 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[ClH:1].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[N:6][O:7][C:8]=2[CH:13]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 13319850HCID 13319850, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 30 ml of dry dimethylformamide, was added 4.2 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 2.0 ml of piperidine, 8.0 g of sodium bicarbonate, and a crystal of potassium iodide. After stirring at 80° C. for two hrs, the mixture was filtered and the filtrate was evaporated to an oil. The oil was stirred with 100 ml of water for five mins and then extracted with ether. The ether extract was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent was evaporated to an oil. The oil was treated with ethereal hydrogen chloride, and the resultant salt was twice recrystallized from ethyl acetate/methanol/ether to give 2.5 g of (42%) product, mp 163°-165° C.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated to an oil
  3. stirringThe oil was stirred with 100 ml of water for five mins
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water (2×), saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customthe solvent was evaporated to an oil
  10. additionThe oil was treated with ethereal hydrogen chloride
  11. customthe resultant salt was twice recrystallized from ethyl acetate/methanol/ether

Sources & evidence

ORD record
ord-8b8fb735f2054d118b001d89b242b5d5
Source dataset
uspto-grants-1986_07
Patent number
US04598152

Reaction notes

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