Chlorotrimethylsilane → Silanamine, N-(phenylmethyl)-N,1,1,1-tetramethyl-

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Reaction Steps

Step 1—To a stirring solution of N-methylbenzylamine (100 ml, 93.9 g, 0.77 mol) in diethyl ether (500 ml) cooled at −78° C. was added n-butyl lithium (2.4 M in hexanes, 355 ml, 0.85 mol) keeping the temperature below −60° C. The resulting slurry was stirred for 1 hour then chlorotrimethylsilane (118 ml, 0.93 mol) was added while keeping the temperature below −70° C. The reaction was allowed to warm to room temperature overnight then filtered to remove the precipitated white solid. The filtrates were concentrated in vacuo then distilled under high-vacuum to yield the N-trimethylsilyl-N-methylbenzylamine (102 g, 94%) as a colorless liquid: b.p. 54° C./0.5 mmHg; 1H NMR (CDCl3) 0.19 (s, 9H), 2.37 (s, 3H), 3.90 (2, 2H) 7.22-7.39 (m, 5H)

Provenance & Evidence