Uses
4-Amino-N,N-dimethylbenzylamine is a reagent in the reaction with methoxycarbonylphenyl isocyanate, in the synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase.
Synthesis
General procedure for the synthesis of 4-dimethylaminomethyl-aniline from N,N-dimethyl-4-nitrobenzylamine: to a solution of N,N-dimethyl-4-nitrobenzylamine (1 g, 5.55 mmol) in acetic acid (10 ml) was added activated iron powder (3 g), and the reaction mixture was stirred for 5 hr at 80 °C. After completion of the reaction, the reaction mixture was filtered; the filtrate was diluted with water and neutralized with 10% sodium hydroxide solution. The product was extracted with ethyl acetate, the organic layers were combined, dried with anhydrous sodium sulfate, filtered and the solvent was evaporated to give the crude product. The crude product was purified by silica gel column chromatography using chloroform/methanol (98:2, v/v) as eluent to give 4-dimethylaminomethyl-aniline (0.7 g, 85% yield).
References
[1] RSC Advances, 2015, vol. 5, # 58, p. 47125 - 47130
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2975 - 2990
[3] Patent: WO2006/123145, 2006, A1. Location in patent: Page/Page column 58
[4] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 257 - 269
[5] Archiv der Pharmazie, 2014, vol. 347, # 12, p. 936 - 949
