Phenylsilane → N-Methyl-1-phenylethylamine

Participants

Reaction Steps

(R,R)-Ethylene-1,2-bis(η5 -4,5,6,7-tetrahydroindenyl) titanium (R)-1,1'-binaphth-2,2'-diolate (53 mg, 0.089 mmol) was dissolved in 4 mL of dry benzene in a Schlenk tube under a nitrogen atmosphere. The tube was wrapped in aluminum foil. A solution of n-butyllithium (72 μL, 0.12 mmol, 1.6M in hexane) was added and the mixture was shaken until it turned a dark red brown color. After 5 min. phenylsilane, (164 μL, 1.33 mmol) was added and the reaction mixture turned blue, then brown, in color. After 10 minutes acetophenone N-methyl imine (119 mg, 0.89 mmol) was added. The tube was shaken and left for about 20 hours at room temperature. The resulting solution was diluted with 15 mL of ether and 3 mL of methanol and allowed to stir for 2 hours. The reaction mixture was then washed with 10 mL of water and extracted with 1M HCl (2×10 mL). The aqueous layer was separated, basified with 5M NaOH (until strongly basic to pH paper), and extracted with ether (3×20 mL). The ether solution was dried over anhydrous sodium sulfate and concentrated to yield 60 mg (0.45 mmol, 50% yield) of N-methyl-1-phenylethylamine as a yellow oil. The yield for repeated experiments ranged from 50 to 80%.

Provenance & Evidence