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Use of the mannich reaction in the synthesis of bispidine
Author(s) -
Ruenitz Peter C.,
Smissman Edward E.
Publication year - 1976
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.5570130539
Subject(s) - chemistry , benzylamine , formaldehyde , yield (engineering) , mannich reaction , condensation , catalysis , organic chemistry , combinatorial chemistry , materials science , physics , metallurgy , thermodynamics
A three‐step synthesis of bispidine ( 1 ) is described. Mannich condensation of N ‐benzyl‐4‐piperidone, formaldehyde, and benzylamine afforded N,N ′‐dibenzylbispidinone ( 5 ), which was reduced under modified Wolff‐Kishner conditions to yield N,N ′ ‐dibenzylbispidine ( 6 ). Catalytic debenzylation of this compound gave 1 .