By Jay Boudreau, Amna Naz
The purpose of this research was to synthesize a lead compound for use as a possible tuberculosis drug. A Grignard addition was performed on 1-bromo-4-chlorobenzene to form 4-(4-chlorophenyl)-1-(phenylmethyl)-4-piperidinol. A separate alcohol, 1-naphthalenemethanol, was chlorinated to 1-(chloromethyl)-naphthalene. Not enough Grignard product was produced, so a deprotected Grignard product was alkylated through an Sn2 reaction with 2-(chloromethyl)-naphthalene to form 4-(4-chlorophenyl)-1-(1-naphthalenylmethyl)-4-piperidinol. A carbon NMR (C-NMR), hydrogen NMR (H-NMR), and IR spectrum were performed on the final product. IR spectrum and C-NMR confirmed the presence of an amine attached to a carbon ring, C-NMR, H-NMR, and IR showed a chlorine connected to a carbon at the correct location, and H-NMR and IR clearly showed aromaticity, with a 1-4 disubstituted aromatic ring as projected. Produced was 0.78 g of product. The results indicate the successful completion of an advanced reaction scheme, producing a product that likely could function as a tuberculosis drug in the future.
