DESOXYCODEINE STUDIES. VI. DESOXYCODEINE-D (DESOXYNEOPINE)¹

Abstract

In the preceding communication (1) it was pointed out that the action of phosphorus pentachloride on dihydropseudocodeine and on dihydroallopseudocodeine resulted in the same 8-chlorodihydrocodide (I). This chloro compound is exceedingly resistant to reduction, but we find that prolonged treatment with sodium in boiling cyclohexanol results in loss of hydrogen chloride, with formation of a new desoxycodeine that we shall designate as desoxycodeine-D. The structure II that we propose for the compound represents it also as the desoxy derivative of the rare opium alkaloid neopine (2). The new desoxycodeine might be logically named desoxyneopine, but this leads to embarrassment in selecting a name for the morphine analog. nch3 I. 8-Chlorodihydrocodide NCHs 1The work reported in this paper is part of a unification of effort by a number of agencies having responsibility for the solution of the problem of drug addiction.

Opiate Dienes as Dienophiles in the Diels−Alder Reaction with 1-Cyano-o-quinodimethane

“…The organic layer was then separated and washed with saturated aqueous NaHCO 3 . The organic layer was dried and evaporated to yield an oil that was chromatographed on a silica gel column (CH 3 OH−CHCl 3 1:20) to yield 8 (182 mg, 44%), mp 58−60 °C (lit . mp 61.2−62 °C), and dihydrodesoxycodiene 13 ( 9 ) (30 mg, 7%), mp 102−106 °C (lit .…”