A Three-Step Synthesis of Fluoxetine

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Her, Kristine; Wollack, James; Bruening, Meaghan
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Fluoxetine is the active ingredient in the antidepressant Prozac. It works as a selective serotonin reuptake inhibitor to treat conditions including depression and obsessive-compulsive disorder. To assemble this molecule, a three-step synthesis was utilized. Intermediates included 1-Propanone, 3-(methylamino)-1-phenyl-(synthesized through an SN2 reaction between 3-Chloropropiophenone and methylamine) and α-[2-(Methylamino) ethyl] benzyl alcohols (synthesized through reduction of the first intermediate using NaBH4). The second intermediate was subjected to 4-chlorobenzotrifluoride and sodium hydride to produce the desired molecule, fluoxetine. In order to make the synthesis more green, the solvent for the second reaction, ethanol, was replaced with water. Over the course of this multi-stage procedure, several synthetic difficulties led to the formation of unexpected products.