Bromine → 6-bromo-1-(1-butylpiperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one
Reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[Br:21]Br>C(O)(=O)C>[Br:21][C:17]1[CH:18]=[CH:19][C:14]2[NH:13][C:12](=[O:20])[N:11]([CH:8]3[CH2:9][CH2:10][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7]3)[C:15]=2[CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-(1-butyl-piperidin-4-yl)-1,3-dihydro-benzimidazol-2-one (0.5 g, 1.38 mmol) was suspended in acetic acid (5 ml) and added bromine (0.07 ml, 1.38 ml) in acetic acid (1 ml). The reaction mixture was stirred at room temperature for 90 minutes, then added water (5 ml) and filtrated, the residue was washed with water, then added ethyl acetate (10 ml) and 1 M sodium hydroxide (aq.) (10 ml). The organic phase was dried with magnesium sulphate and evaporated to dryness. The residue was chromatographed on kieselgel 60 and eluted with ethyl acetate/methanol (7/3 (v/v)). The product fractions was evaporated to a foam. Yield 40 mg (0.1 mmol, 8%). M.p. 179-181° C.