Benzylamine → 2-(benzylamino)acetonitrile

Participants

Reaction Steps

To a stirred solution of glycollonitrile (25 g) in methanol was added dropwise over 45 minutes benzylamine (46.9 g) keeping the temperature of the reaction between 15°-20°. Following the addition the reaction mixture was kept overnight at room temperature, and then distilled to give benzylaminoacetonitrile (42.0 g) as a colourless oil, b.p. 120°/15 mm. Reaction of this (3.0 g) with 3,5-dimethylbenzoyl chloride (3.46 g) was described above gave crude N-benzyl-3,5-dimethylbenzoylaminoacetonitrile (5.81 g) as a colourless viscous oil which was used in the next stage without further purification. To this crude amide (2.0 g) in anhydrous methylene chloride (8 ml) was added sulphuryl chloride (0.97 g). Following the cessation of gas evolution (ca. 15 min.), anhydrous methanol (20 ml) and finely powdered anhydrous potassium carbonate (1.95 g) was added to the mixture which was then stirred for 30 minutes. Solids were removed from the solution which was then evaporated and the residual oil chromatographed on a column of silica using methylene chloride as an eluent. Following elution from the column and evaporation of the solvent, the product (1.2 g) was obtained as a very pale-yellow viscous oil.

Provenance & Evidence