Simple preparation of new N-aryl-N-(3-indolmethyl) acetamides and their spectroscopic analysis

Abstract

Objectives. To prepare new indolic molecules and characterize them by spectroscopic methods. Materials and methods: All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were monitored by thin layer chromatography over Silufol UV 254 0.25 mm-thick chromatoplates. Product isolation and purification were performed by column chromatography (SiO 2), using ethyl acetate-petroleum ether mixtures as eluents. Results. The synthesis of new N-aryl-N-(3indolmethyl) acetamides based on first step iminization reaction of indol-3-carbaldehyde is accomplished. The structures of the C-3 substituted indoles were confirmed by 1 H-NMR and 13 C-NMR studies supported by inverse-detected 2D NMR experiments and also through monocrystal X-ray diffraction. Conclusions. An efficient, economic, and fast synthetic route was designed to the construction of the N-aryl-N-(3-indolmethyl) acetamides, structural analogues of some alkaloids.

Chromatography and Its Applications

“…The method employed to obtain the precursor 7, is one of the most known procedures to reduce an aldimines with an excess of NaBH 4 in methanol, protocol that is still the reaction of choice to produce secondary amines in reasonably good yield. Thus, N- (2-cyanophenyl)-N-(3-indolylmethyl)amine 7 is prepared as was described and was obtained as white solid in 70 % yield after purification through recrystallization (Bello et al, 2010). This example, in which the main precursor is prepared in a linear process and purified by recrystallization, represents an excellent technique that avoids the loss of value material and it will be increase the global yields of the final product.…”

Simple Preparation of New Potential Bioactive Nitrogen-Containing Molecules and Their Spectroscopy Analysis

“…The method employed to obtain the precursor 7, is one of the most known procedures to reduce an aldimines with an excess of NaBH 4 in methanol, protocol that is still the reaction of choice to produce secondary amines in reasonably good yield. Thus,amine 7 is prepared as was described and was obtained as white solid in 70 % yield after purification through recrystallization (Bello et al, 2010). This example, in which the main precursor is prepared in a linear process and purified by recrystallization, represents an excellent technique that avoids the loss of value material and it will be increase the global yields of the final product.…”