Synthesis of Prozac (Fluoxetine)

Prozac (Fluoxetine) is a widely used antidepressant belonging to the class of selective serotonin reuptake inhibitors (SSRIs). It increases serotonin levels in the brain by inhibiting its reabsorption, which helps improve mood and treat depression, anxiety disorders, and OCD.

 

 

 

In this exercise, add the missing reagents and draw the structures of the intermediates in the synthesis of Fluoxetine. The preparation of fluoxetine incorporates several key reactions from different chapters of organic chemistry:

  • Electrophilic Aromatic Substitution (EAS) – used to introduce substituents onto the aromatic ring.

  • Nucleophilic Aromatic Substitution (SNAr) – used to replace an activated aromatic leaving group with a nucleophile.

  • The Mannich Reaction – an amine–formaldehyde–carbonyl condensation covered in the chapter on Reactions of Enols and Enolates (alpha carbon chemistry).

Together, these steps illustrate how multiple reaction classes come together in the multistep synthesis of an important pharmaceutical compound.

 

Practice

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