Synthesis of Quatenary Ammonium Compounds from Eugenol through Mannich and Methylation Reactions and Its Antibacterial Activity

Abstract

6-[(N-iodo-N-methyl-N-methyl-N-methylamino)methyl]-4-alyl-2-methoxyphenol was synthesized through Mannich and methylation reaction. Mannich reaction was carried out by reacting eugenol, formaldehyde 37%, and dimethylamine 40% with ethanol at temperature of 78°C for 90 minutes and 4-allyl-6(dimethylamino)methyl-2-methoxyphenol was obtained with yield of 83,03%. Quartenary ammonium salt, 6-[(N-iodo-N-methyl-N-methyl-N-methylamino)methyl]-4-allyl-2-methoxyphenol, was obtained through methylation reaction of 4-allyl-6-(dimethylamino)methyl-2-methoxyphenol with methyl iodide in ethanol. In the FTIR spectrum, the specific peak of ammonium salt was exhibited at 948.98 and 455.20 cm-1. The antibacterial activity of 6-[(N-iodo-N-metil-N-methyl-N-methylamino)methyl]-4-allyl-2-methoxyphenol was performed against E. coli and S. aureus, this quaternary ammonium salt exhibited a strong activity.