[Intramolecular aromatic alkylation. 24. Synthesis and pharmacologic testing of...

Demethylation of 1a,b is achieved by trichloroethyl chloroformate via the carbamates 1d,f to yield the secondary bases 1e,g which are realkylated directly by selected alkyl halogenides (route A) or via the acid amides 1k,m by LiAlH4-reduction (route B) to give 1h,i,o and 1l,n respectively. Pharmacological examination indicates substance 1a to be a powerful molecule in the writhing test, whereas substitution of the aromatic moiety and exchange of the N-methyl group in 1b,c,i diminish the activity distinctly.