Potassium Hydroxide → 3-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

HRID 969734Notes

Reaction equation

HRID 969734 reaction equation
Cl.F[C:3]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:4]=1[C:5](=[N:12][OH:13])[CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[OH-].[K+]>O>[F:18][C:16]1[CH:15]=[CH:14][C:4]2[C:5]([CH:6]3[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]3)=[N:12][O:13][C:3]=2[CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57357481Methanone, (2,4-difluorophenyl)-4-piperidinyl-, oxime, hydrochloride (1:1)

Product 1

HCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 11 g of 4-(2,4-difluoro-benzoyl)piperidine-oxime hydrochloride and 25 g of potassium hydroxide in 25 ml of water is heated to boiling with stirring for 2 hours. The reaction mixture is cooled to room temperature and extracted with toluene. The organic phase is dried over anhydrous sodium sulfate and evaporated in vacuo. The residual crude product is recrystallized from petroleum ether. Thus 7.1 g of the title compound are obtained. According to HPLC MS analysis the product contains 5% of 4-{6-[4′-(6′-fluoro-1′,2′-benzisoxazol-3′-yl)-piperidine-1′-yl]-1,2-benzisoxazol-3-yl}-piperidine, as a contamination (compound of the Formula VI).

Workup

  1. temperatureis heated
  2. extractionextracted with toluene
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customThe residual crude product is recrystallized from petroleum ether

Sources & evidence

ORD record
ord-403354407f654bdea74d5597e06528d4
Source dataset
uspto-grants-2007_12
Patent number
US07307168B2

Reaction notes

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