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A PROCESS FOR PREPARING PURE 3-[2-[4-(6-FLUOROBENZO[D]ISOXAZOL-3-YL)-1-PIPERIDYL]ETHYL]-7-HYDROXY-4-METHYL-1,5-DIAZABICYCLO[4.4.0]DECA-3,5-DIEN-2-ONE

IP.com Disclosure Number: IPCOM000199487D
Publication Date: 2010-Sep-06
Document File: 1 page(s) / 14K

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A PROCESS FOR PREPARING PURE 3-[2-[4-(6-

FLUOROBENZO[D]ISOXAZOL-3-YL)-1-PIPERIDYL]ETHYL]-7-HYDROXY-4-

METHYL-1,5-DIAZABICYCLO[4.4.0]DECA-3,5-DIEN-2-ONE

3-[2-[4-(6-fluorobenzo[d]isoxazol-3-yl)-1-piperidyl]ethyl]-7-hydroxy-4-methyl-1,5- diazabicyclo[4.4.0]deca-3,5-dien-2-one, is a 5-HT antagonist belonging to the chemical class of benzisoxazole derivatives and a racemic mixture having the following structural formula:

OH

Provided is a process the preparation of pure 3-[2-[4-(6-fluorobenzo[d]isoxazol-3-yl)- 1-piperidyl]ethyl]-7-hydroxy-4-methyl-1,5-diazabicyclo[4.4.0]deca-3,5-dien-2-one by using a metal complexant:
225-300 lit of Acetonitrile,12 Kg of 6-fluoro-3-piperidino-1,2-benisoxazol HCl, 10.8-
12 Kg of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrrido[1,2-a]- pyrimidin-4-one and 0.75-1.66 Kg of sodium carbonate and a complexant are charged into a 400 lit reactor. The reactor is then inertized with nitrogen and then the suspension is bubbled with nitrogen for at least 1 hr.

The suspension is heated to 60-reflux and stirred at 60-reflux at least 20 hr until the reaction is ended. The suspension is then cooled to 2-15ºC, stirred for at least 0.5 hr, filtered (in 500 lit filter dryer) and washed with acetonitrile. The obtained cake is then slurried in water, filtered and washed until neutral pH is achieved. The obtained cake is then dissolved in 720:1080 lit of Acetone: Water mixture (3:1) at 55ºC-reflux.

The solution is transferred to 1000 lit re...