Desipramine → 3-{[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-methyl-amino}-propionic Acid Ethyl Ester

Participants

Reaction Steps

A solution of 6.02 g (19.8 mmol) of desipramine hydrochloride was allowed to stir at room temperature for 5 minutes. This was extracted with 6×100 ml of chloroform. The combined organic part was washed with 100 ml of water, dried with anhydrous Na2SO4 and concentrated to give 5.25 g of desipramine free base. A solution of 2.82 g (10.6 mmol) of desipramine free base in 100 ml of anhydrous acetone was added. To this reaction mixture 2.03 ml (15.8 mmol) of ethyl-3-bromopropionate, 3.65 g (26.4 mmol) of anhydrous potassium carbonate, 264 mg (1.76 mmol) of sodium iodide, 5 mg of 18-crown-6 and 0.7 ml of anhydrous DMF were added. The reaction mixture was allowed to reflux under argon overnight. The mixture was filtered and the residue was washed with 20 ml of acetone. The combined filtrate was concentrated and purified by silica gel column chromatography using 4% methanol in ethyl acetate to give 3.45 g (9.41 mmol, 89%) of the ethyl ester (17) as a thick oil.

Provenance & Evidence