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

HRID 280891Notes

Reaction equation

HRID 280891 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. for 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 (2x), 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 (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 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-4eb6e9b12e734731a1217bb0d4049eef
Source dataset
uspto-grants-1986_05
Patent number
US04591586

Reaction notes

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