TITLE:
Synthesis of N-Benzyl-3-anilinopropanamides and Cyclization to 4-Hydroxy-4-N-benzylamino-1,2,3,4-tetrahydroquinoline
AUTHORS:
Lami A. Nnamonu, Vincent C. Agwada, Chukwuemeka A. Nwadinigwe
KEYWORDS:
3-Anilinopropanamide; N-Benzylanilinopropanamide; 1, 2, 3, 4-Tetrahydroquinoline
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.3 No.4,
December
4,
2013
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.