D. Perrine, J. T. Ross, S. Nervi
Nov 1, 2000
Citations
1
Influential Citations
50
Citations
Journal
Journal of Chemical Education
Abstract
A one-pot synthesis of (±)-2-(t-butylamino)-3'-chloropropiophenone (bupropion) as its hydrochloride salt (Zyban, Wellbutrin), an important antidepressant drug used in the treatment of nicotine addiction, is described. The procedure, suitable for students in their first year of organic chemistry, can be carried out in less than two hours and provides material of high purity in overall yield of 75-85%. A solution of m-chloropropiophenone in CH2Cl2 is treated with Br2. After removal of the solvent, t-butylamine and N-methylpyrrolidinone are added and the mixture is warmed briefly, quenched with water, and extracted with ether. Concentrated HCl is added to the ether solution to precipitate the product.