Chemistry 251 Laboratory -- Spring 2001
Piperine Project Home Page

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Last updated on 2/12/01


Synthesis of Piperine

Faculty Mentor: Tim Hoyt

Reference: Sloop, J.C. J. Chem. Ed. 1995, 72, A25-A27.

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.

Students Working on This Project

Lab Day Name E-mail
Monday Janie Marples
Monday Rachel Chambers
Tuesday Maria Diss
Tuesday Rachel Rhymes
Wednesday Ryan Moline
Wednesday Billy Nugent
Thursday Aft. Erika Juergensen
Thursday Aft. Adam Willard
Thursday Eve. Kristina Haley
Thursday Eve. Mary Kotschwar

Table of Reagents and Amounts Available for this Project

The table below lists the chemicals that we will have available for this project. If you need something that is not on this list, consult with the mentor for your project. Also note the "Amount/group" column. This is the total amount of material available for each group to use on the project.
Reagent Source Amount/group Location Comments
Methyl crotonate Aldrich
Cat. # 13,945-9
10 mL TA room
N-Bromosuccinimde Aldrich
Cat. # B8,125-5
10 g TA room
Benzoyl Peroxide, 97% Aldrich
Cat. # 17,998
1 g Fridge (50 g bottle) Caution: Benzoyl peroxide should be handled with care. Use a plastic spatula when transferring.
Triethyl phosphite Aldrich 1 g TA Rooom
Piperonal Aldrich 1 g TA Rooom
Sodium methoxide Aldrich 2 g TA Rooom
Oxalyl chloride Aldrich
Cat. # 0-880-1
2 mL TA Rooom Be sure to use pure oxalyl chloride, not the 2M oxalyl chloride in dichloromethane. Work in the hood, and dispense the oxalyl chloride under nitrogen.
Piperidine Aldrich 2 mL TA Rooom