The Synthesis of N-(( 4-bromo-3-(4 –cholorophenyl)isoxazol-5-yl)metyl)cyclopentanamine

Isoxazole derivatives are interesting heterocyclic compounds since they show a wide range of pharmacological properties including anti-inflammatory, anti-cancer, anti-bacerial, and anti-viral activities [1].There is an obvious demand for brominated isoxazoles due to their importance both as synthetic intermediates and pharmacological targets [2]. This research work describes the synthesis of new compound of isoxazole family. First, 4-choloro benzaldehyde (1) was transformed to 4-choloro benzaldoxime (2) by using NH2OH in pyridine. The in situ generated nitriloxide from reaction between (2) and NaOCl, in a cycloaddition procedure, then was reacted with propargylalcohol to produce 3-(4-choloro phenyl)-5-hydroxymethyl isoxazole (3). Compound (4) was prepared by reaction of Br2 and compound (3) in CH2Cl2 to produce 3-(4-bromo)-4-cholorophenyl-5-(hydroxymethyl)isoxazole(4).Then, compound (4) reacted with PBr3 in CH2Cl2, to produce 3-(4-bromo)-4-choloro phenyl-5-(bromo methyl)- isoxazole (5). The final compound was obtained by addition of Et3N and cyclopentylamine in presence of benzene to produce N-((4-bromo-3-(4 –cholorophenyl)isoxazol-5-yl)metyl)cyclopentanamine(6). The structure of all the synthesized compounds was characterized and confirmed by FT-IR and NMR spectroscopy techniques.