Benzylamine → 1-Benzyl-4-methyl-4-phenyl-[1,4]azasilinane

Participants

Reaction Conditions

Reaction Steps

8.5 g of 2-[(2-hydroxy-ethyl)-methyl-phenyl-silanyl]-ethyl alcohol is put in 80 ml of anhydrous dichloromethane under nitrogen. 14.2 ml of triethylamine is added, and then, at 0° C., 6.9 ml of mesyl chloride is added dropwise using a dropping funnel. The mixture is stirred for 2 h at 0° C. and gradually turns orange with appearance of a precipitate. Once conversion is complete, 14.2 ml of triethylamine is added and then 4.7 ml of benzylamine at 0° C. The reaction mixture is brought back to room temperature and then refluxed for 6 h. After hydrolysis with H2O at room temperature, the reaction mixture is extracted with ethyl acetate three times. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated under vacuum. The raw product obtained is chromatographed on silica gel, eluting with a gradient of ethyl acetate and heptane containing 3% of triethylamine varying from 0/10 to 3/7. 3.6 g of 1-benzyl-4-methyl-4-phenyl-[1,4]azasilinane is obtained in the form of a clear yellow oil.

Provenance & Evidence