By Anna Dube, Summerlin Gates

Faculty Mentor: Davis Oldham

Abstract

The purpose of this lab was to synthesize 4-piperidinol, 4-(4-bromophenyl)-1-(2-naphthalenylmethyl)-(9Br, ABr), a drug to treat tuberculosis. To a solution of thionyl chloride and chloromethane chloride, we gradually added 2-napthalene methanol to chloromethane chloride and heated and refluxed and rotor evaporated. To confirm it worked, we ran a TLC plate in a solvent of 3:1 heptane ethyl acetate and an NMR. We suspended that product and piperidin-4-one in acetonitrile, added sodium carbonate and refluxed for 5 hours while stirring and then rotor evaporated to get proper product. Next, after that product was confirmed to have worked using NMR and another TLC plate, 2-methyltetrahydrofuran and 1,4 dibromo benzene was added dropwise to a solution of magnesium turnings, 2-methyltetrahydrofuran, and iodine. That was refluxed for two hours and then hydrolyzed using ammonium chloride and was followed by an extraction using ethyl acetate and dried over sodium carbonate. After doing a mass spectroscopy of the product, the peaks viewed determined that the Grignard step of the reaction didn’t produce the proper product. The results were inconclusive due to some peaks aligning with the intended product, but others not.