1,1,1-Trichloroethane → [3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid methyl ester

Participants

Reaction Steps

Desipramine hydrochloride (1 equivalent, 0.3 gram) was added drop wise to a stirred solution of potassium carbonate (2 equivalents, 0.27 gram) in dry DMF at 0° C. Methyl chloroform (1.2 equivalents, 0.1 ml) which had been dissolved in dry DMF was added drop wise to this mixture and stirred for 6 hours at room temperature. The reaction mixture was quenched with water, extracted with ethyl acetate, the organic layer separated, washed with brine solution and dried over anhydrous sodium sulfate. The dried material was concentrated and purified by column chromatography to provide a pale yellow liquid (yield: 0.18 gram) and analyzed by HPLC (purity 97.7%). The FTIR, MS and 1H NMR spectra were consistent with the assigned with the empirical formula of C20H24N2O2.

Provenance & Evidence