The Synthesis Investigation of N-((3-4-chorophenyl)isoxazol-5-yl)methyl)cyclopentanamine

Compounds with isoxazole moiety have pharmacological, biological and industrial applications, specifically these compounds show antiviral activity [1]. Recently, the synthesis of isoxazole 4- and 5-carbaldehydes and their conversion to isoxazolyl-1,4-dihydropyridines were studied [2]. In this research work, the nitration of N-((3-4-chorophenyl)isoxazol-5-yl)methyl)cyclopentanamine is investigated.First, 4-chlorobenzaldehyde (1) was transformed to 4-chlorobenzaldoxime (2) by using NH2OH in pyridine. The in-situ generated nitriloxide from reaction between 2 and NaOCl, was reacted with propargylalcohol to produce (3-(4-chlorophenyl)isoxazol-5-yl)methanol (3) in a cycloaddition procedure. Then compound 3 at the presence of Br2 in CH2Cl2 gave 5-(bromomethyl)-3-(4-chlorophenyl)isoxazole (4).Then, The final product obtained from reaction of compound (4) and cyclopentylamine. The structure of all the synthesized compounds was characterized and confirmed by FT-IR and NMR spectroscopy techniques.