Potassium Iodide → HCID 13319852, compound

HRID 745319Notes

Reaction equation

HRID 745319 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][CH2:14][CH2:15][CH2:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=2[O:19][N:18]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[ClH:13].[F:26][C:24]1[CH:23]=[CH:22][C:21]2[C:17]([CH2:16][CH2:15][CH2:14][N:10]3[CH2:9][CH2:8][CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:12][CH2:11]3)=[N:18][O:19][C:20]=2[CH:25]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 698734-PhenylpiperidineHCID 516892Sodium BicarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 13319852HCID 13319852, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 30 ml of dry dimethylformamide was added 2.4 g of 4-phenylpiperidine, 3.4 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 8.0 g of sodium bicarbonate, and a few crystals of potassium iodide. After stirring at 100° C. for three hrs, the mixture was filtered and the filtrate was evaporated to an oil. The oil was stirred with 100 of ml water for five mins and then extracted into 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 dissolved in ether and treated with ethereal hydrogen chloride, and the resultant salt was twice recrystallized from ethyl acetate/methanol/ether to give 3.0 g (53%) of product, mp 213°-214° C.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated to an oil
  3. stirringThe oil was stirred with 100 of ml water for five mins
  4. extractionextracted into 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. dissolutionThe oil was dissolved in ether
  11. additiontreated with ethereal hydrogen chloride
  12. customthe resultant salt was twice recrystallized from ethyl acetate/methanol/ether

Sources & evidence

ORD record
ord-13804d90665c4644b0548e1c2de21427
Source dataset
uspto-grants-1986_07
Patent number
US04598152

Reaction notes

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