Trihexyphenidyl is a medication used in the treatment of Parkinson’s disease, a movement disorder with a variety of motor and non-motor symptoms. While the exact biochemical mechanism of trihexyphenidyl remains ambiguous, it is estimated that the compound acts on the parasympathetic nervous system directly through the inhibition of acetylcholine. Additionally, trihexyphenidyl is marketed as a racemic mixture. Our project is focused on the synthesis of racemic trihexyphenidyl and subsequent resolution into its two enantiomers. The key convergent chemical step in the synthesis is a Grignard reaction and resolution will take place using classical separation of diastereomeric salts. The synthesis, resolution, characterization, and approaches to biological testing of the enantiomers will be described.

Synthesis and chemical resolution of 1-cyclohexyl-1-phenyl-2-piperidylethanol (Trihexyphenidyl<sup>®</sup>)

ACS Spring 2022

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Synthesis and chemical resolution of 1-cyclohexyl-1-phenyl-2-piperidylethanol (Trihexyphenidyl®)

Synthesis and chemical resolution of 1-cyclohexyl-1-phenyl-2-piperidylethanol (Trihexyphenidyl^®)