Date of Award
Spring 2026
Degree Type
Honors College Thesis
Academic Program
Chemistry BS
Department
Chemistry and Biochemistry
First Advisor
Dr. Matthew Donahue
Advisor Department
Chemistry and Biochemistry
Abstract
Piperidine is a heavily utilized nitrogen containing heterocycle found in numerous pharmaceutical agents, solidifying its importance as a building block in drug development. The focus of this research is to investigate different mechanisms of action for adding and replacing various functional groups utilizing readily available lab materials. These findings would lead to determining the overall influence of substitution patterns and functional groups have on stereochemistry, reactivity, and overall conformation of the piperidine ring. The synthetic approach involves the formation of 3-bromo-5-methoxy-tosylpiperidine intermediate through acid promoted cyclization, followed by nucleophilic substitution reactions to introduce various functional groups. Reaction progress and product formation were monitored using thin layer chromatography, and nuclear magnetic resonance spectroscopy and infrared analysis were utilized to characterize structures. The work evaluates how cis, trans, and geminal substitution patterns affect transition states and product outcomes, which provides insight into stereochemical control during piperidine formation.
Copyright
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Recommended Citation
Monroe, Teyanna, "SYNTHESIS OF PIPERIDINE HETEROCYCLES WITH SPECIFIC FUNCTIONAL GROUPS VIA SN2 REACTIONS" (2026). Honors Theses. 1091.
https://aquila.usm.edu/honors_theses/1091