Potassium Iodide → 3-Dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate

Participants

Reaction Steps

In dimethylformamide (30 ml), 3-(3-acetoxy-4-acetyl-2-propylphenoxy)propylbromide (1.6 g) was allowed to react with 3-dimethylaminopropyl 3-bromo-4-hydroxybenzoate.hydrochloride (1.7 g), potassium iodide (0.83 g) and potassium carbonate (0.7 g) at 60°-70° C. for 6 hours with stirring. Insoluble materials were filtered off, and the filtrate was concentrated. The resulting syrup was purified by means of a flash chromatography using silica-gel to give 3-dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate (1.8 g). The product was dissolved in ether, to which was added equivalent oxalic acid (250 mg) to give crystalline oxalate (1.8 g), m.p. 141°-142° C.

Provenance & Evidence