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1998
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October
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In the Laboratory
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Synthesis of NMP, a Fluoxetine (Prozac) Precursor, in the Introductory Organic Laboratory
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Daniel M. Perrine, Nathan R. Sabanayagam, and Kristy J. Reynolds
Department of Chemistry, Loyola College in Maryland, Baltimore, MD 21210-2699
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October 1998
Vol. 75 No. 10
p. 1266
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| Abstract |
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A synthesis of the immediate precursor of the widely used antidepressant fluoxetine (Prozac) is described. The procedure is short, safe, and simple enough to serve as a laboratory exercise for undergraduate students in the second semester of introductory organic chemistry and is one which will be particularly interesting to those planning a career in the health sciences. The compound synthesized is (±)-N,N-dimethyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine, or "N-methyl Prozac" (NMP). The synthesis of NMP requires one two-hour period and a second three-hour period. In the first period, a common Mannich base, 3-dimethylaminopropiophenone, is reduced with sodium borohydride to form (±)-3-dimethylamino-1-phenylpropanol. In the second period, potassium t-butoxide is used to couple (±)-3-dimethylamino-1-phenylpropanol with p-chlorotrifluoromethylbenzene to form NMP, which is isolated as its oxalate salt. All processes use equipment and materials that are inexpensive and readily available in most undergraduate laboratories. Detailed physical data are given on NMP, including high-field DEPT 13C NMR.
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| Supplement |
Detailed versions of the laboratory experiment are available for the instructors and students. They can be accessed as PDF files which requires Acrobat Reader to view. The supplement has also been compressed into Zip and Sit files.
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| More Information |
Citation |
Perrine, Daniel M.; Sabanayagam, Nathan R.; Reynolds, Kristy J. J. Chem. Educ. 1998 75 1266.
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Keywords |
laboratory instruction, organic chem, drugs, pharmaceuticals, industrial chem, medicinal chem, synthesis
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History |
Created:
Last Updated: |
June 21, 1999
November 22, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
1998
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October
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1266
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