Sloop, J.C. J. Chem.
Piperine is a component of black pepper which causes sneezing.
Its presence in pepper was discovered many years ago, and its structure was elucidated near the beginning of the century. The synthesis starts with an allylic, radical halogenation to introduce a bromine atom. An Arbuzov reaction with triethyl phosphite displaces the bromine and produces a phosphonate that is then coupled to piperonal using a modified Wittig reaction. Hydrolysis of the ester, formation of the acid chloride using oxalyl chloride, and coupling to piperidine completes the synthesis. The table below lists the chemicals that we will have available for this project.