Reaction #2329088

Reaction equation

Water

Potassium carbonate

benzyl bromide

1-(2-fluoro-4-nitrophenyl)-[1,4]diazepane hydrochloride

→

title compound

1-benzyl-4-(2-fluoro-4-nitrophenyl)-[1,4]diazepane

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   WashThe organic layer was washed with saturated brine
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   OtherThe residue obtained by evaporation of the solvent under reduced pressure
5. 5
   Otherwas purified by column chromatography on silica gel (methanol ethyl acetate=1:1)

Procedure

Potassium carbonate (0.526 g, 3.80 mmol) and benzyl bromide (0.155 ml, 0.130 mmol) were added to a solution of 1-(2-fluoro-4-nitrophenyl)-[1,4]diazepane hydrochloride (compound of Reference Example 55; 0.300 g, 1.08 mmol) in anhydrous N,N-dimethylformamide (6 ml), and the mixture was stirred at 80° C. for 6 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (methanol ethyl acetate=1:1) to give the title compound (0.248 g, 69%) as a brown liquid.

Source