2,4,6-Trimethylbenzylamine

Chemical Properties

Synthesis Reference(s)

Synthesis

1585-16-6

40393-99-5

A. Synthesis of 2,4,6-trimethylbenzylamine: To a solution of 2,4,6-trimethylbenzyl chloride (5 g, 29.7 mmol) in DMSO (20 mL) was added sodium azide (2.9 g, 44.6 mmol). The reaction mixture was heated at 60 °C with stirring for 3 h. After completion of the reaction, it was cooled to room temperature and poured into water (200 mL). The resulting precipitate was collected by filtration and dissolved in wet THF (50 mL) followed by the addition of triphenylphosphine (15.6 g, 59.4 mmol). The mixture was heated to reflux and maintained for 3 hours. At the end of the reaction, the volatiles were removed by evaporation. The residue was dissolved in 1N HCl (200 mL) and the insoluble material was removed by filtration. The filtrate was alkalized and the resulting precipitate was collected by filtration and finally dried under vacuum to give 2,4,6-trimethylbenzylamine (2.7 g, 61% yield).

References