Dibenzylamine → Tert-butyl 2-[(dibenzylamino)methyl]prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(bromomethyl)propenoic acid t-butyl ester (20 g, 90.5 mmole) in dry acetonitrile (360 ml), cooled to 0° C., was treated with solid potassium carbonate (15.63 g, 113 mmole), followed by a solution of dibenzylamine (17.83 g, 90.5 mmole), in dry acetonitrile (600 ml), producing a 10° C. exotherm. The reaction was stirred at 0° C. for 0.5 hours, followed by 1 hour at room temperature, and then partitioned between water and diethyl ether. The ether phase was washed again with water, dried (sodium sulphate) and evaporated to yield the crude product (31 g) which was filtered through a pad of silica, eluting with hexane/CH2Cl2 (1:1), to yield 2-(dibenzylaminomethyl)propenoic acid t-butyl ester (23.8 g, 78%) as a solid, m.p. 62°-63° C. Found: C,78.09; H,8.20; N,4.18. C22H27NO2 requires C,78.3; N,8.06; N,4.15 %.

Provenance & Evidence