Collect. Czech. Chem. Commun. 1991, 56, 1725-1731

6-(6-Substituted amino-2-hydroxypropyl)-5,6,7,8-tetrahydrodibenz[c, e]azocines

Fridrich Szemesa, Alfonz Rybárb,*, Pavol Hrnčiarc, Eva Solčániovác and Ondrej Gattnára

a Drug Research Institute, 900 01 Modra
b Institute of Chemistry, Slovak Academy of Sciences, 842 38 Bratislava
c Department of Organic Chemistry, Comenius University, 842 15 Bratislava


Nucleophilic addition of alkyl-, cycloalkylamines, or saturated nitrogen-containing heterocycles to isolated or in situ generated 6-(2,3-epoxypropyl)-5,6,7,8-tetrahydrodibenz[c,e]azocine (III) afforded 6-(3-substituted amino-2-hydroxypropyl)-5,6,7,8-tetrahydrodibenz[c,e]azocines IV and their hydrochlorides. The starting 5,6,7,8-tetrahydrodibenz[c,e]azocine (I) reacted with 1-chloro-2,3-epoxypropane to yield 6-(3-chloro-2-hydroxypropyl)-5,6,7,8-tetrahydrodibenz[c,e]azocine (II), which, on treatment with sodium ethoxide or an excess of an amine eliminated hydrogen chloride to give the intermediate III.