Rapid and simple synthesis of secondary aromatic amines under solvent-free phase transfer catalytic conditions

In this study, we report an efficient synthesis method of various secondary aromatic amine derivatives. Secondary anilines containing aromatic structure, which are valuable intermediates broadly used in the manufacturing of pharmaceuticals, dyestuffs, synthetic rubbers, herbicides, etc. A reaction of meta-substituted primary anilines with non and para-methyl substituted benzyl chlorides, catalyzed by tetrabutylammonium bromide as a phase transfer catalyst in solvent-free condition under microwave irradiation, has been developed. A frequently used processing technique employed in microwave-assisted organic synthesis involves solvent-less procedure was established with many advantages, including mild reaction conditions, short reaction times, simple work-up procedures, moderate to good yields and eco-friendly approach. The target compounds (1-18), were obtained in moderate to good yields (26-65 %). The obtained H-1 NMR, C-13 NMR and mass spectroscopic data are in accordance with the predicted structures. It is likely that the developed procedure can give an easy accession to synthesize various intermediate secondary amine products in future studies.