Potassium Iodide → 8-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-1,4-dioxa-8-azaspiro[4.5]decane hydrochloride

HRID 1248489Notes

Reaction equation

HRID 1248489 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[Cl:11][CH2:12][CH2:13][CH2:14][C:15]1[C:19]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=2[O:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:11].[F:24][C:22]1[CH:21]=[CH:20][C:19]2[C:15]([CH2:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:6][CH2:7]3)=[N:16][O:17][C:18]=2[CH:23]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole

Product 1

HCID 233157868-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-1,4-dioxa-8-azaspiro[4.5]decane hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15 g of 1,4-dioxa-8-azaspiro-[4.5]decane, 25 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 29 g of potassium carbonate and a few crystals potassium iodide in 80 ml of dimethylformamide was stirred at 70°-75° C. in two 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 (2×), saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was treated with ethereal hydrogen chloride to give 18 g (48%) or product, mp 170°-173° C. Recrystallization from ethyl acetate/methanol gave the analytical sample, mp 178°-179° 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 18 g (48%) or product, mp 170°-173° C
  11. customRecrystallization from ethyl acetate/methanol
  12. customgave the analytical sample, mp 178°-179° C.

Sources & evidence

ORD record
ord-749a08fdd8644ce2908811f6ae80bd81
Source dataset
uspto-grants-1985_06
Patent number
US04524209

Reaction notes

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