Boron tribromide → HCID 69497965, compound

HRID 460654Notes

Reaction equation

HRID 460654 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21]C)[N:10]=[C:9]1[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[N:10]=[C:9]1[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69497767HCID 69497767, compound

Product 1

HCID 69497965HCID 69497965, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

3-Benzyl-3,5-dihydro-5-(2′-methoxybenzylidene)-2-methylimidazol-4-one (1.38 g) was dissolved in dichloromethane (20 ml) and boron tribromide (1.3 ml) was added dropwise while stirring the mixture at −40° C. Thereafter, the mixture was stirred under ice-cooling for 1 hr, poured into ice water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3-benzyl-3,5-dihydro-5-(2′-hydroxybenzylidene)-2-methylimidazol-4-one (1.14 g) as red crystals. The crystals and (S)-glycidyl nosylate (1 g) were dissolved in dimethylformamide (20 ml) and potassium carbonate (1.1 g) was added. The mixture was heated at 50° C. for 2 hr, poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oily product (1.05 g). This oily product and 4-(naphthalen-2-yl)piperidine were dissolved in methanol (10 ml) and refluxed under heating for 2 hr. After cooling, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (0.25 g) as an oil.

Workup

  1. stirringThereafter, the mixture was stirred under ice-
  2. temperaturecooling for 1 hr
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-352ea8aba3d1483787e23c3cbb12c641
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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