Phenylacetic Acid → N-Benzyl-2-phenylacetamide

Participants

Reaction Steps

Into a 25 mL round bottom flask equipped with a stir bar was added phenyl acetic acid (0.075 g, 0.55 mmol, 1.1 equiv), (2-iodo-5-methoxyphenyl)boronic acid (13.9 mg, 0.05 mmol, 10 mol %) and 1 g of activated 4 Å Molecular Sieves. Dichloromethane (7 mL) was added and the mixture was stirred for 10 min. Then, benzylamine (55 pit, 0.5 mmol, 1 equiv) was added (in order to get reproducible results, it is necessary to use a gas tight 100 μL syringe). The resulting mixture was stirred for 2 h at room temperature (24-25° C.). The reaction mixture was filtered through a pad of Celite® 545, the filtrate was washed with aqueous acidic solution (pH=4), aqueous basic solution (pH=10-11) and brine. The organic layer was collected, dried over anhydrous Na2SO4 and evaporated to yield the title compound (71% using 1, 98% using 2) as a pure product. The catalyst can be recuperated in up to 80% yield by acidification of the aqueous basic solution to pH 7 and extraction with EtOAc.

Provenance & Evidence