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

HRID 241584Notes

Reaction equation

HRID 241584 reaction equation
Cl.F[C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:11][OH:12].[OH-].[K+]>>[F:9][C:7]1[CH:6]=[CH:5][C:4]2[C:10]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:11][O:12][C:3]=2[CH:8]=1

Participants

3

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 75%

Procedure

2,4-difluorophenyl-(4-piperidinyl)-methanone oxime hydrochloride (5.52 g, 20 mmol) is added to 25 ml of 50% potassium hydroxide; reflux for 4 hours, cooled to room temperature, and extracted with toluene (25 ml×2). The combined organic phases are dried over anhydrous magnesium sulfate, filtered, evaporated to dryness under reduced pressure, and recrystallized in diethyl ether, to obtain 3.3 g of a product, with a yield of 75%.

Workup

  1. temperaturereflux for 4 hours
  2. extractionextracted with toluene (25 ml×2)
  3. dry with materialThe combined organic phases are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customrecrystallized in diethyl ether

Sources & evidence

ORD record
ord-d1fad0c25b314da899d8a6cf9cd11778
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Reaction notes

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