PITHECOLOBINE, THE ALKALOID OF PITHECOLOBIUMSAMAN BENTH. I

Abstract

Pithecolobine, C22H46N4O2, has a lactam group, one primary and two secondary amino groups, and a hydroxyl group. Lithium aluminum hydride converts it into a monocyclic saturated compound, desoxypithecolobine, C22H48N4. Hofmann degradation of this compound gives tetramethylputrescine, trimethyl amine, a doubly unsaturated base C16H31N with a terminal methylene group, and a base C16H34N2. Heating with selenium yields a hydrocarbon, C12;H24–26, with a sequence of six or more CH2 groups. A crystalline oxygen-free compound with two nitrogens (m.p.94 °C.) is also obtained, the ultraviolet spectrum of which is almost identical with aminopyridine.