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Synthesis of 7‐azadispiro[5.1.5.2]pentadecane and 6‐azadispiro[4.1.5.2]tetradecane
Author(s) -
Wagner E. R.,
Matthews D. P.
Publication year - 1984
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.5570210509
Subject(s) - pentadecane , chemistry , tetradecane , hydrochloride , cyclohexene , organic chemistry , hydrocarbon , catalysis
Two new, hindered secondary amines, 7‐azadispiro[5.1.5.2]pentadecane hydrochloride ( 1a ) and 6‐azadispiro[4.1.5.2]tetradecane hydrochloride ( 1b ), have been prepared in four steps from 1‐ethynylcyclohexylamine ( 2 ). The final thermal cyclization of 1‐(2‐(1‐aminocyclohexyl)ethyl)cyclohexyl chloride ( 5a ) produces 1‐(2‐(1‐aminocyclohexyl)ethyl)cyclohexene hydrochloride ( 6a ) and an unsaturated hydrocarbon 7 in addition to 1a .