Butaclamol
Butaclamol is a type of antipsychotic which was never marketed. Sold as the hydrochloride salt for use in research, the compound acts as a dopamine receptor antagonist.
Discussion
pKa = 7.15is an analog of butaclamol. is also described in the attached article. This is similar to McN 4612-z except it is the opposite optical antipode. It is therefore supposedly an antipsychotic.
Synthesis
The synthesis has been reported: Patent:- The starting material is made by a Favorskii reaction of dibenzosuberone with acetylene followed by a Meyer–Schuster rearrangement to the aldehyde and oxidation to the acid. Another method is Reformatsky reaction with bromoethylacetate and catalytic hydrogenation of the olefin in the ester that follows dehydration.
- The starting material is called 10,11-Dihydro-5H-dibenzo-cycloheptene-5-acetic acid, PC12669091. FGI by any of a number of methods to the isocyanate gives. Addition of one equivalent of water gives N-formyl-10,11-dihydro-5H-dibenzocycloheptene-5-methylamine. Cyclization gives 1,7,8,12b-tetrahydrobenzocycloheptisoquinoline . A modified Robinson annulation with methylvinylketone gave PC21397166.