Process for preparing carboline derivatives and compounds used in their

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.