Acetonitrile → 1,2-Benzisoxazole

HRID 1069302Notes

Reaction equation

HRID 1069302 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]2[C:6](C3CCNCC3)=[N:7][O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].BrCCCO.C(#N)C>O>[O:8]1[C:4]2[CH:3]=[CH:2][CH:16]=[CH:15][C:5]=2[CH:6]=[N:7]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 710731,2-Benzisoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (10.0 g, 45 mmol), K2CO3 (10.0 g), 3-bromo-1-propanol (7.3 g, 46 mmol) and acetonitrile (200 ml) was refluxed for 3 hours. The reaction was poured into H2O and 7.1 g of a beige solid was collected. The filtrate was extracted with dichloromethane, and after concentration an additional 6.7 g of crude solid was harvested. The solids were combined and triturated with refluxing ethyl acetate to afford 8.0 g of 6-fluoro-3-1-(3-hydroxypropyl)-4-piperidinyl]-1,2-benzisoxazole as an off-white solid. A sample (4.0 g) was recrystallized from ethanol-water (with charcoal treatment) to yield 2.4 g (40%) of the alcohol as a white solid, m.p.=140-142° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customwas collected
  3. extractionThe filtrate was extracted with dichloromethane
  4. concentrationafter concentration an additional 6.7 g of crude solid
  5. customtriturated with refluxing ethyl acetate

Sources & evidence

ORD record
ord-76b92dc075f147acaae8e9e97854e167
Source dataset
uspto-grants-2001_06
Patent number
US06251907B1

Reaction notes

Loading…