Desipramine → {2-[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propylamino]-ethyl]-carbamic Acid tert-butyl Ester

Participants

Reaction Steps

To 3.23 g (12.04 mmol) of desipramine free base was added 80 ml of dry acetone, 3.6 g of anhydrous potassium carbonate, 3.0 g (13.45 mmol) of 2-(BOC-amino) ethyl bromide, 3 ml of anhydrous dimethylformamide, 15 mg of 18-crown-6 and 500 mg of sodium iodide. The mixture was allowed to reflux 18 hours under argon atmosphere. The reaction mixture was cooled to room temperature and filtered. The residue was washed with 10 ml of acetone. The filtrate was concentrated and the residue was purified by silica gel column chromatography using 4% methanol in ethyl acetate to give 4.8 g (11.7 mmol, 96%) of 23 as a thick oil.

Provenance & Evidence