By Abaigeal Higgins & Molly Ryan Gates

Faculty Mentor: Dr. Davis Oldham

Abstract

The purpose of this lab was to propose and perform a sequence of reactions to create a target molecule that could be used to cure tuberculosis using a pre-selected list of reactions including reactants. First, thionyl chloride, 1-napthalenemethanol, and CH2Cl2 were gradually mixed in an ice bath, refluxed for 1 hour, and then rotary evaporated to form 2-chloromethylnapthalene. 1.25grams of 2-chloromethylnapthalene was produced supported by NMR & TLC. Second, 2-chloromethylnapthalene was refluxed with 2-butanone and 4-pepierdone monohydrate hydrochloride for 18 hours with a rotary evaporation in-between and after producing 1-(2-napthylmethyl) piperdione. 1.84grams product of which roughly 60% desired product, proved by GmassSpec & TLC. Third, 2-methyl THF, magnesium, and iodine were refluxed together for 4 hours as a mixture of 1-bromo-4-chlorobenzene and THF was added, 1/3 at first with the rest being dropwise though a separatory funnel. A mix of 1-(2-napthylmethyl) piperdione and THF was added after cooling. After, NH4Cl was added to the mixture followed by water and ethyl acetate. The layers were separated, and the organic layer was dried over magnesium sulfate, gravity filtrated and vacuum filtrated. A GmassSpec was taken, and results were inconclusive in determining if desired product was produced.