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Chapter 6
Synthesis of benzodiazepines
General synthesis of 1-substituted-5-(4-fluorophenyl)-1H-benzo[e]
[1,4]diazepin-2(3H)-one (ADZ-04a-j).
To solution of 5-(4-fluorophenyl)-1H-beno[e][1,4]diazepin-2(3H)-one (0.0039
mol) in DMF (10 ml), potassium hydroxide (0.0046 mol) and appropriate alkyl halide
(0.0039 mol) were added at 0 o C. The reaction mixture was stirred for 3-5 h at this
temperature. The progress of reaction was monitored by thin layer chromatography.
After completion of reaction mixture, it was poured into cold water. The solid
separated was filtered, washed with water and dried. The crude product was
recrystallized from ethanol to give analytical pure product in 79-90% yield.
General synthesis of 3-benzylidene-5-(4-fluorophenyl)-1Hbenzo[e][1,4]diazepin-2(3H)-one
(ADZ-05a-j)
5-(4-Fluorophenyl)-1H-beno[e][1,4]diazepin-2(3H)-one (0.0039 mol),
potassium hydroxide (0.0039 mol) and appropriate aromatic aldehydes (0.0039 mol)
were taken in toluene (20 mL). The reaction mixture was heated to reflux for 8-10 hrs.
The progress of reaction was monitored by thin layer chromatography. After
completion of reaction mixture cooled to room temperature and the solid separated
product was filtered, washed with cold toluene and dried. The crude product was
recrystallized from ethanol to give corresponding product ADZ-05a-j in 80-94% yield.
Department of Chemistry, Saurashtra University, Rajkot-360005 217