Synthesis of a Dual Serotonin Reuptake Inhibitor/Histamine H₃ Antagonist

Significance

A common side effect to the use of serotonin reuptake inhibitors as antidepressants is the persistance of cognitive impairment and fatigue, even as mood improves. Histamine H₃ inhibitors improve cognition and increase wakefulness. The target molecule inhibits both serotonin reuptake and histamine H₃ thereby offering an imroved treatment for depression. A salient feature of the synthesis is the rare use of a Friedel-Crafts alkylation of a benzylic alcohol to generate the di­arylmethane motif.