Author(s)

Lami A. Nnamonu, Vincent C. Agwada, Chukwuemeka A. Nwadinigwe

Department of Chemistry, University of Agriculture, Makurdi, Nigeria.
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria.

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.

 

 

3-Anilinopropanamide; N-Benzylanilinopropanamide; 1, 2, 3, 4-Tetrahydroquinoline

L. Nnamonu, V. Agwada and C. Nwadinigwe, "Synthesis of N-Benzyl-3-anilinopropanamides and Cyclization to 4-Hydroxy-4-N-benzylamino-1,2,3,4-tetrahydroquinoline," International Journal of Organic Chemistry, Vol. 3 No. 4, 2013, pp. 229-234. doi: 10.4236/ijoc.2013.34032.