Toluene → 2-[2-(Methyl-2-propyn-1-ylamino)ethyl]-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

A mixture of bromoethylphthalimide (20.23 g, 0.080 mol), N-methyl-N-propargyl amine (5.0 g, 0.072 mol), potassium carbonate (17.5 g, 0.126 mol), and toluene (80 ml) was refluxed for 8 hours, filtered and the insoluble material washed with toluene. After removal of the solvent, the residue was purified by flash chromatography (Merck 60 silica gel, step gradient from pure dichloromethane to 4% methanol in dichloromethane). The pure fractions were combined, evaporated under reduced pressure, dried in vacuo to provide 16.24 g of title product.

Provenance & Evidence