Potassium Iodide → HCID 13319856, compound

HRID 745321Notes

Reaction equation

HRID 745321 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.[CH2:15]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:1].[CH2:15]([CH:22]1[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=3[O:7][N:6]=2)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 13319856HCID 13319856, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5 g 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 5 g of 4-benzylpiperidine, 10 g of potassium carbonate and a few crystals potassium iodide in 50 ml of dimethylformamide was stirred at 70° for 4.5 hr. The mixture was cooled, filtered and concentrated to an oil. The oil was stirred with water and extracted with ether. The organic extracts were washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was treated with ethereal hydrogen chloride to give a salt. The salt was immediate rebasified to give an oil, which was purified by column chromatography (silica gel, tetrahydrofuran). The purified oil was treated with ethereal hydrogen chloride, and the resultant salt was recrystallized from ethyl acetate/methanol to give 2.8 g (31%) of product, mp 188°-189° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to an oil
  4. extractionextracted with ether
  5. washThe organic extracts were washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe residue was treated with ethereal hydrogen chloride
  10. customto give a salt
  11. customto give an oil, which
  12. customwas purified by column chromatography (silica gel, tetrahydrofuran)
  13. additionThe purified oil was treated with ethereal hydrogen chloride
  14. customthe resultant salt was recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-ef1271127bff41d6a5cb8aeb5d7778b8
Source dataset
uspto-grants-1986_07
Patent number
US04598152

Reaction notes

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