Sodium Hydroxide → N-(2-pyrazinylmethyl)-3-chloropropionamide

Participants

Reaction Steps

To an aqueous solution of sodium hydroxide (2.31 g) in water (30 ml) was added 2-aminomethylpyrazine hydrochloride (7.0 g) under ice cooling, to which 3-chloropropionylchloride (5.05 g) and solution of sodium hydroxide (2.31 g) in water (30 ml) were simultaneously added dropwise over 30 minutes under stirring. The mixture was stirred for 1 hour at room temperature, followed by extraction with ethyl acetate-THF (1:1, 100 ml×2). The aqueous layer was subjected to salting out with sodium chloride, followed by extraction with ethyl acetate-THF (1:1, 100 ml×2). The organic layers were combined and dried over magnesium sulfate, followed by concentration under reduced pressure. The concentrate was subjected to column chromatography [carrier: silica gel, 200 g; developing agent: ethyl acetate→ethyl acetate-ethanol (4:1)]. The eluent was concentrated and the resulting solid was washed with hexane to give the title compound (4.50 g) as colorless solid product.

Provenance & Evidence