Synthesis of piperidine analogs of 1-(3- chlorophenyl)piperazine, a well known serotonin ligand

Article abstract of DOI:10.1002/jhet.5570360431

Synthesis of arylpiperideines 3a-3d and arylpiperidines 4a- 4d as analogs of a well known serotonin ligand 1-(3- chlorophenyl)piperazine is reported. Starting aryllithium derivatives were treated with 1-methyl-piperdin-4-one to provide the corresponding hydroxy derivatives 6a and 6b. N- Methylpiperideine derivatives 3a and 3c were obtained by their dehydration while the corresponding N-unsubstituted compounds 3b and 3d were prepared indirectly by a three-step procedure. Hydrogenation of piperideine 3a provided the corresponding piperidine derivative 4a which after demethylation yielded 4b. Similar 4-pyridyl derivatives 4c and 4d were prepared by a similar strategy via the corresponding methoxy derivatives.