Synthesis of new 4-aryl-1-(biarylmethylene)piperidines. Structural analogs of adoprazine (SLV313)

Abstract

A series of new 4-aryl-1-(biarylmethylene)piperidines have been synthesized. They are structurally related to SLV-313, a potential atypical antipsychotic agent with potent D2 receptor antagonist and 5-HT 1A receptor agonist properties. Suzuki-Miyaura reaction of cyclic vinyl boronates, derived from the vinyl triflates of N-protected tetrahydropyridines, with appropriate aryl halides yielded 4-arylpiperidines. The reductive amination of the latter with suitable biarylaldehdyes accomplished the synthesis of the new compounds. © 2012 Verlag der Zeitschrift für Naturforschung.