Tiagabine hydrochloride

Tiagabine hydrochloride is an anticonvulsant, which blocks GABA uptake into presynaptic neurons, allowing more GABA to be available for binding with the GABA receptor of postsynaptic cells. It is effective as an adjunctive treatment for partial seizures. 

Acid-catalyzed hydrolysis with aqueous hydrochloric acid was a facile process the hydrochloride salt of the product could be crystallized out of the same solution. 0.15 N hydrochloric acid was found to be optimally effective in cleaving the ester without ra-cemizing the chiral center. The methods developed here were general ones that could be adapted to the synthesis of several analogs of tiagabine. 

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