Acetic Acid → 4-methyl-7-Dimethylamino-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of intermediate 3 (3.0 g, 13 mmol) and 37% aq formaldehyde (21 mL, 0.26 mol) in acetonitrile at 0° C., NaBH3CN (4.8 g, 77 mmol) was added portionwise. The reaction mixture was stirred at 0° C. for 2 h and then at room temperature for 1 h. Acetic acid (1.4 mL) was then added and the reaction mixture was stirred for another 2 h. The reaction mixture was poured into ethyl ether, washed with 2N KOH and the basic layer was extracted several times with ethyl acetate. The organic phases were collected and dried and solvents removed in vacuum to give an amorphous yellowish solid.

Provenance & Evidence