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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D261-02
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classificationIPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D261-04
http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D261-02
filingDate 1997-07-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1998-06-02-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_739ad1e73f0a75577bde1a35ac75dab2
publicationDate 1998-06-02-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-5760243-A
titleOfInvention Preparation and use of 2-methyl-5-phenylisoxazolidine
abstract (a) An alkali metal base (hydroxide, oxide, carbonate, bicarbonate or sesquicarbonate), an acid addition salt of N-methylhydroxylamine, and (iii) water are mixed together to form a reaction mixture in which the acid of the acid addition salt has been neutralized. (b) Reaction mixture from (a) and formaldehyde or formalin are mixed together and the resultant mixture is subjected to reaction conditions that produce a reaction mixture in which N-methylnitrone has been formed. (c) Reaction mixture from (b) and styrene are mixed and the resultant mixture to subjected to reaction conditions that produce a reaction mixture in which 2-methyl-5-phenylisoxazolidine has been formed. Preferably, 2-methyl-5-phenylisoxazolidine formed in (c) is hydrogenated such that N-methyl-3-phenyl-3-hydroxypropylamine is formed, which in turn is reacted with 4-halobenzotrifluoride such that N-methyl-3-phenyl-3- 4-trifluoromethyl)phenoxy!propylamine is formed. Conversion of the N-methyl-3-phenyl-3- 4-trifluoromethyl)phenoxy!propylamine to its racemic hydrochloride salt provides fluoxetine hydrochloride, a widely used antidepressant.
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