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Synthesis of <i>N</i>-Benzyl-3-anilinopropanamides and Cyclization to 4-Hydroxy-4-<i>N</i>-benzylamino-1,2,3,4-tetrahydroquinoline
Department of Chemistry, University of Agriculture, Makurdi, Nigeria
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
- 1 Department of Chemistry, University of Agriculture, Makurdi, Nigeria
- 2 Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
- 3 Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
International Journal of Organic Chemistry·Volume 03 (2013)·Pages 229–234·Published 4 December 2013·DOI10.4236/ijoc.2013.34032
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Abstract
Substituted 3-anilinopropanamides were converted to N -benzyl derivatives via uncatalyzed amine exchange reaction with benzylamine in up to 41% yield. Unprotected aniline nitrogen had been observed to inhibit facile cyclization. An attempt was therefore made to protect the N by acetylation prior to cyclization. During this process, facile ring closure occurred in the methoxy series to give 4-hydroxy-4- N -benzylamino-1,2,3,4-tetrahydroquinolines in up to 69% yield.
Keywords3-Anilinopropanamide<i>N</i>-Benzylanilinopropanamide1234-Tetrahydroquinoline
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