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Synthesis of piperidine analogs of 1‐(3‐chlorophenyl)piperazine, a well known serotonin ligand
Author(s) -
Rádl Stanislav,
Hezký Petr,
Taimr Jan,
Proška Jan,
Krejčí Ivan
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360431
Subject(s) - chemistry , piperidine , piperazine , ligand (biochemistry) , derivative (finance) , demethylation , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , receptor , biochemistry , gene expression , dna methylation , financial economics , economics , gene
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.