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http://dx.doi.org/10.1248/cpb.13.211

has been cited by the following article:

• 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.