N-alkyl-14-hydroxymorphinans and derivatives
US4161597A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Dec 20, 1976 |
| Grant date | Jul 17, 1979 |
| Priority date | — |
| Expiry date | Dec 20, 1996 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D489/08
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
There is provided a novel and high yield procedure for transforming acid salts of 14-alkanoyloxymorphinans and derivatives thereof into the corresponding N-alkyl-14-hydroxymorphinans wherein the alkyl moiety on the nitrogen contains the same number of carbon atoms as that previously in the 14-alkanoyl moiety. In the process of the present invention, the acid is neutralized to the free base, the alkanoyl moiety at the 14-oxy then spontaneously shifts to the nitrogen and is subsequently reduced to the corresponding alkyl moiety. O-dealkylation at C-3, where an alkoxy group is originally present, is carried out in the usual manner. There is also provided a readily produced and readily disassociated adduct of the corresponding 14-hydroxy-N-alkanoyl morphinan-6-alkylene ketal with benzene, tetrahydrofuran, and the like.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.