Triethylamine → HCID 66591171, compound

Participants

Reaction Steps

(3-(Trifluoromethyl)phenyl)methanamine (25 g, 143 mmol), (chloromethyl)trimethylsilane (19.92 mL, 143 mmol), and triethylamine (23.87 mL, 171 mmol) were combined neat and the resultant mixture was refluxed overnight. The reaction was cooled to room temperature and 150 mL of heptane was added. The HCl salts were removed by filtration and washed with heptane. The solvent was removed by placing under house vacuum and then high vacuum. N-(3-(Trifluoromethyl)benzyl)-1-(trimethylsilyl)methanamine was isolated by vacuum distillation (bp 70-90° C./3.2 torr): 1H NMR (300 MHz, CDCl3) δ ppm 7.59 (s, 1H), 7.53-7.38 (m, 3H), 3.86 (s, 2H), 2.04 (s, 2H), 1.34 (s, 1H), 0.06 (s, 9H).

Provenance & Evidence