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

Article abstract of DOI:10.1016/S0040-4020(01)96616-5

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 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 and subsequent modification to 7,12-dihydro-3H-[2]-benzoxepino[4,3-e]indole. Standard procedures were then used to construct the dimethylaminoethyl side chain to yield the title compound.