Abstract
The structures of doxepin and serotonin were overlayed using molecular graphics and 1 - [2-(dimethylamino)ethyl] - 7, 12 - dihydro - 3H - [2] - benzoxepino[4,3-e]indole( 1) was proposed as a potential antidepressant agent. This paper deals with the synthesis of the title compound. Key steps in the synthesis include a regioselective electrophilic substitution at C-4 of ethyl 5-hydroxy-1-indolecarboxylate ( 4) and subsequent modification to 7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole( 12). Standard procedures were then used to construct the dimethylaminoethyl side chain to yeild the title compound ( 1).
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