GB773467A - Morphine alkaloids - Google Patents

Abstract

The invention comprises: (a) a substance designated "neopinone" of the formula: <FORM:0773467/IV(b)/1> and its acid addition salts and chloroform solvate complex; (b) the preparation of neopinone by treating 14-bromocodeinone with hydrogen in the presence of a hydrogenation catalyst and a neutral solvent (preferably in the presence of a noble metal, especially a supported palladium catalyst, and a lower aliphatic alcohol); (c) the conversion of neopinione to codeinone by heating (preferably in admixture with activated charcoal in a medium comprising ethyl acetate); (d) the reduction of neopinone to neopine by means of an alkali metal borohydride (defined as a boron compound in which an alkali metal is associated with a group consisting of a boron atom and 1-4 reactive hydrogen atoms and in which, when there are fewer than 4 hydrogen atoms, the group containing the boron atom may contain 1-3 univalent atoms other than hydrogen or 1-3 univalent radicals, or a combination thereof, said atoms or radicals being relatively inert and non-reactive with respect to the reducing action of the hydrogen atoms). In examples: (1) and (3) 14-bromocodeinone is treated with hydrogen in the presence of palladium-on-charcoal in benzene/methanol and benzene/chloroform/methanol respectively; (2) neopinone is reduced with NaBH4 in methanol; (4) and (5) neopinone is refluxed with activated charcoal in ethyl acetate under slight nitrogen pressure. Salts of neopinone mentioned are the hydrochloride, hydrobromide (formed initially in the hydrogenolysis reaction), citrate, tartrate and sulphate).ALSO:A violet dye having the formula <FORM:0773467/IV(b)/1> is produced by treating neopinone (see Group IV(b)) with methyl iodide and adding aqueous alcohol to the resulting methiodide. The reaction is preferably effected under nitrogen and is accelerated by the addition of a weak base. The dye may be purified by chromatography on Florisil.