3-Chloropropionyl chloride → 5-(3-chloro-propionyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

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The synthesis was performed according to the below synthetic scheme. To a solution of 11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4] diazepin (0.376 gr., 1.79 mmol) in dry THF, (10 ml) NaNH2 (0.132 gr., 3.39 mmol) was added. The mixture was cooled to 0° C., and 0.2 ml 3-chloropropionyl chloride (2.09 mmol) was added dropwise. The mixture was stirred for 30 min at 0° C., allowed warming to room temperature, washed with 5% aq. potassium bicarbonate and extracted with CH2Cl2 (20 ml). The resulting organic layer was dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was crystallized from ether, resulting in 0.467 gr. (87% yield) of 11-Oxo-10,11-dihydro-5-[(3-chloro)1-oxopropyl] 5-H-dibenzo[b,e] [1,4] diazepin in the form of a yellow solid, mp 241-242° C. 1H NMR (CDCl3): 8.78 (s, 1H), 7.98 (s, 1H), 7.59 (s, 1H), 7.4-7.26 (m, 6H), 3.77 (m, 4H). FAB/MS: 301(M+).

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