Process for converting neopinone to codeinone
AssigneeThe Regents of the University of California
InventorsHenry Rapoport, Randy B. Barber
Life of this patent
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Abstract
A process for converting neopinone alkaloid to codeinone alkaloid which involves treating neopinone with a hydrohalic acid in a suitable solvent under anhydrous conditions. It also relates to the compound 8-halodihydrocodeinone hydrohalide.
Claims14
A compound represented by the following formula:
- ##STR2## wherein X is a halogen selected from the group consisting of chlorine, bromine and iodine.
A process for preparing codeinone which involves
- A. reacting neopinone or a mixture containing neopinone and codeinone with a hydrohalic acid selected from the group consisting of hydrochloric, hydrobromic and hydroiodic under anhydrous conditions to form the corresponding 8-halodihydrocodeinone hydrohalide,
- B. treating the 8-halodihydrocodeinone hydrochloride with a basic agent to form codeinone.
A process for preparing codeinone which involves
- A. reacting a solution of neopinone or a mixture containing neopinone and codeinone in methylene chloride with hydrobromic or hydrochloric acid in diethyl ether under anhydrous conditions at a temperature of from about 0.degree. C. to about 30.degree. C. to form the corresponding 8-halodihydrocodeinone hydrohalide, said hydrobromic or hydrochloric acid being present in an amount of from about 2 to 4 moles per mole of neopinone.
- B. treating the 8-halodihydrocodeinone hydrochloride with sodium hydroxide so that the pH of the final mixture containing codeinone is from about 8 to 13.
A process for preparing 8-halodihydrocodeinone hydrohalide which comprises reacting neopinone or a mixture containing neopinone and codeinone with a hydrohalic acid selected from the group consisting of hydrochloric, hydrobromic and hydroiodic under anhydrous conditions to form the corresponding 8-halodihydrocodeinone hydrohalide.
Dependencies are inferred from the claim text.