Bromine → HCID 21262759, compound

HRID 567784Notes

Reaction equation

HRID 567784 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]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 45496423-(1-butylpiperidin-4-yl)-1H-benzimidazol-2-one

Product 1

HCID 21262759HCID 21262759, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

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.

Workup

  1. filtrationadded water (5 ml) and filtrated
  2. washthe residue was washed with water
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. customevaporated to dryness
  5. customThe residue was chromatographed on kieselgel 60
  6. washeluted with ethyl acetate/methanol (7/3 (v/v))
  7. customThe product fractions was evaporated to a foam

Sources & evidence

ORD record
ord-5eb634f47cbc45798560e14bcc82b913
Source dataset
uspto-grants-2001_01
Patent number
US06180649B2

Reaction notes

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