- A new industrial process for oxcarbazepine
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A novel industrial process for the antiepileptic drug oxcarbazepine 1 has been developed. Unlike the old process, the new process is free from halogenated solvents and can be performed in standard production equipment. It starts from commercially available 1,3-dihydro-1-phenyl-2H-indol-2-one 10. In the key step, an electrophilic ring closure reaction of 2-[(methoxycarbonyl)phenylamino] benzeneacetic acid 5 to 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester 6 in poly phosphoric acid was applied. For the manufacture of 5, a highly efficient process using a dianion strategy was developed.
- Fuenfschilling, Peter C.,Zaugg, Werner,Beutler, Ulrich,Kaufmann, Daniel,Lohse, Olivier,Mutz, Jean-Paul,Onken, Ulrich,Reber, Jean-Louis,Shenton, David
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p. 272 - 277
(2012/12/24)
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- A new synthesis of oxcarbazepine using a Friedel-Crafts cyclization strategy
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A novel, simple, and straightforward process for the large-scale synthesis of oxcarbazepine, the active ingredient of Trileptal, a medicine for the treatment of epilepsy, has been developed. Starting from readily available 1,3-dihydro-1-phenyl-2H-indol-2-one, a Friedel-Crafts cyclization strategy provides a direct route to the tricyclic framework of the target molecule. Crucial to the success of the strategy was the choice of the proper nitrogen-protecting group.
- Kaufmann, Daniel,Fünfschilling, Peter C.,Beutler, Ulrich,Hoehn, Pascale,Lohse, Olivier,Zaugg, Werner
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p. 5275 - 5278
(2007/10/03)
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