Title: Synthesis of 2,5-substituted piperidines and their bicyclic piperazine analogs - the 2,7-substituted octahydro-2h-pyrido[1,2-a]pyrazines
Authors: Compernolle, Frans ×
Saleh, Ma
Toppet, Suzanne
Hoornaert, Georges #
Issue Date: Jan-1991
Publisher: Amer chemical soc
Series Title: Journal of Organic Chemistry vol:56 issue:17 pages:5192-5196
Abstract: Partial and complete reduction of the key compound 1-benzyl-5-(ethylenedioxy)-2-piperidinecarbonitrile (1) was applied to generate the corresponding aldehyde 2 and primary amine 3. These were transformed into bicyclic 7-(ethylenedioxy)-2(R)-octahydro-2H-pyrido[1,2-a]pyrazines 7 (R = H) and 15 (R = aryl) through the following sequence: (i) chloroacetylation of 3 and of arylamines derived from 2, (ii) cyclization to give the intermediate lactams 5 and 14, and (iii) reduction with LiAlH4. Deprotection of the N-aryl compounds 15 yielded the corresponding ketone model compounds 16. From amino acetal 7, a complementary ketone synthon 11 was prepared via N-benzylation and cleavage of the acetal group, providing a general route to piperidine-bridged analogues of 1,4-substituted piperazine drugs.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Chemistry - miscellaneous
× corresponding author
# (joint) last author

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