Process for preparing carboline derivatives and compounds used in their preparation
US4451655A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | May 17, 1982 |
| Grant date | May 29, 1984 |
| Priority date | — |
| Expiry date | May 17, 2002 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D471/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A novel process for preparing various 2-substituted-5-aryl-1,2,3,4-tetrahydro-.gamma.-carboline derivatives is provided, which involves (1) quaternizing a corresponding 5-aryl-.gamma.-carboline compound with an appropriate aralkyl halide in the presence of sodium iodide, followed by (2) reduction of the corresponding quaternary carbolinium iodide salt intermediate with an alkali metal hydride to yield the desired final product. The latter compounds are known to be useful as tranquilizing agents, with 2-[4-(p-fluorophenyl)-4-hydroxybutyl]-5-(p-fluorophenyl)-8-fluoro-1,2,3,4- tetrahydro-.gamma.-carboline representing a preferred final product. The aforesaid carbolinium salt intermediates as well as the corresponding 5-aryl-.gamma.-carboline starting materials are all novel compounds.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.