Potassium Iodide → HCID 13319858, compound

HRID 280887Notes

Reaction equation

HRID 280887 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.[CH3:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:1].[CH3:15][CH:16]1[CH2:21][CH2:20][N:19]([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)[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 693814-MethylpiperidineHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 13319858HCID 13319858, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 2.9 g of 4-methylpiperidine, 10 g of potassium carbonate and a few crystals potassium iodide in 50 ml of dimethylformamide was stirred at 65°-70° C. for four hrs. 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 (2x), saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was treated with ethereal hydrogen chloride to give 4 g (55%) or product, mp 180°-182° C. Recrystallization from ethyl acetate/methanol gave the analytical sample, 189°-190° 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 (2x), 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 4 g (55%) or product, mp 180°-182° C
  11. customRecrystallization from ethyl acetate/methanol
  12. customgave the analytical sample, 189°-190° C.

Sources & evidence

ORD record
ord-ae463842109f4d6ea24984adc574630b
Source dataset
uspto-grants-1986_05
Patent number
US04591586

Reaction notes

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