Synthese und Hofmann-Abbau des 1-(Diphenyl-hydroxymethyl)-2,2-dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisochinolinium-Ions

Abstract

Summary. The synthesis of the N-quaternary aminoalcohol 6 is described. Analogous to the
aminoalcohols 1 and 2, 6 on treatment w i t h alkali undergoes fission of the substituent at C(l) as a
carbonyl compound, with formation of a N, N-dimethyl-l,2,3,4-tetrahydroisoquinolinium ion,
which is further degraded to the corresponding o-vinyl-benzylamine {Scheme 7). - As a by-product
of a Bischler-Napieralski ring closure, we observed chlorination of an aromatic ring (yielding 19).