The synthesis of 1-[2-(dimethylamino)ethyl]-7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole : A potential antidepressant agent

The structures of doxepin and serotonin were overlayed using molecular graphics and 1 - 2-(dimethylamino)ethyl] - 7, 12 - dihydro - 3H - 2] - benzoxepino4,3-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]-benzoxepino4,3-e]indole(12). Standard procedures were then used to construct the dimethylaminoethyl side chain to yeild the title compound (1).