SYNTHESIS OF N-{[7-METHOXY-2-(4-METHOXYPHENYL)-1-BENZOFURAN -5-YL]METHYL}CYCLOPENTANAMINE BY REDUCTIVE AMINATION Synthese von N-{[7-METHOXY-2-(4-methoxyphenyl)-1-BENZOFURAN -5-yl] methyl} cyclopentanamine durch reduktive Aminierung

Vanillin (1) undergoes sequence of reaction forming phosphonium salt through dimethyaminomethyl derivative (Mannich reaction). The synthesis of phosphonium salt can be achieved by sequence of three steps. A solution of amino compound in acetic anhydride was refluxed for 24 hrs to give crude diacetate which is purified and reacted with HCl to give chloromethyl derivative. It is reacted with triphenylphosphine in dry benzene under reflux condition. The phosphonium salt undergoes condensation with 4-methoxybenzoyl chloride by refluxing in toluene in presence of triethylamine (Wittig reaction). The resulting 7-methoxy-2-[4- (methoxy)phenyl)-l-benzofuran-5-carboxaldehyde (4) was subjected to reductive amination and the final product N-{[7-methoxy-2-(4-methoxyphenyl)-1-benzofuran-5- yl]methyl}cyclopentanamine (5) was purified by column chromatography and characterized by NMR and Mass spectroscopy.