6,7-Benzomorphans have been reported to show
pronounce n a r c o t i c analgesic activities. In proceeding
years several compounds comprising 6,7-benzomorphan
nucleus have been synthesized. Previous works were
c e n t r e d mainly on structure- activity relationship to the
effective of oxygen, hydroxide, alkyd or aryl s u b s t i t u e n t s on
various p o s i t i o n s of the molecule and v a r i a t i o n of
N - s u b s t i t u e n t s .
The present work is concerned with t h e synthesis of
6,7-benzomorphan having an amino group at C-9 of the
molecule. The s y n t h e s i s of the t i t l e compound involved
bromination and rearrangement of h e t e r o c y c l i c enamines,
followed by aqueous basic hydrolysis to give 9-oxobenzomorphan.
Conversion of 9-oxo compound to the oxime
followed by c a t a l y t i c reduction afforded the desired
9o(-amino-6,7-benzomorphan. Its pharmacology demonstrated
a dose-dependent i n h i b i t i o n analgesia.
The product obtained as well as the intermediates
have been analyzed and c h a r a c t e r i z e d on the basis of thier
spectrial and chemical properties