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In the Laboratory
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A Short, One-Pot Synthesis of Bupropion (Zyban®, Wellbutrin®)
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Daniel M. Perrine, Jason T. Ross, Stephen J. Nervi, and Richard H. Zimmerman
Department of Chemistry, Loyola College in Maryland, Baltimore, MD 21210-2699
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November 2000
Vol. 77 No. 11
p. 1479
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| Abstract |
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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.
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| Supplement |
Instructions for students, a guide for the instructor, and FTIR, 1H NMR, 13C NMR, and DEPT data are available.
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 Contents |
JCE2000p1479W.wpd (Word Perfect 9, Windows)
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| More Information |
Citation |
Perrine, Daniel M.; Ross, Jason T.; Nervi, Stephen J.; Zimmerman, Richard H. J. Chem. Educ. 2000 77 1479.
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Keywords |
Drugs / Pharmaceuticals; Industrial Chemistry; Laboratory Instruction; Medicinal Chemistry; Organic Chemistry; Organic Synthesis
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History |
Created:
Last Updated: |
October 6, 2000
August 31, 2005
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November
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1479
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