1958 Volume 78 Issue 9 Pages 974-977
Boiling of norepinephrine or N-methylepinephrine with hydrochloric acid respectively afforded 2, 3, 7, 8-tetrahydroxy-5-aminomethyldibenzo [a, e] cyclohepta-1, 4, 6-triene hydrochloride (I), m.p. 316-318° (decomp.), and 2, 3, 7, 8-tetrahydroxy-5-dimethylaminomethyl-dibenzo-[a, e] cyclohepta-1, 4, 6-triene hydrochloride (II), m.p. 268-270° (decomp.), in respective yields of ca. 15% and ca. 20%. The ultraviolet spectra of their aqueous solution were similar to that of adnamine. Methylation of (I) and (II) with dimethyl sulfate and alkali hydroxide gave the same methosulfate of m.p. 264°, which was found to be identical with methyladnamine methosulfate by mixed fusion and from ultraviolet spectra. Similar decomposition of 1-monoalkoxyphenyl-2-alkylaminoethanols failed to give compounds possessing a dibenzocycloheptatriene ring, resulting in recovery of the starting material in meta-substituted compounds and complete decomposition in para-substituted compounds to form a large amount of carbohydrates.
