反应详情

To 15 mL of MeCN was added 880 mg (4.99 mmol) of N-benzyl-piperazine and 1.16 g (5.00 mmol) of 1,2-dimethyl-isothiourea hydroiodide. The mixture was heated at reflux overnight. Then, 970 mg (5.02 mmol) of 2-bromo-3-isopropoxy-propenal and 2.07 g (15.0 mmol) of K2CO3, and 250 mg of 18-crown-6 were added and the mixture was heated to reflux overnight. The mixture was cooled, concentrated, and dissolved in EtOAc with a small amount of water to dissolve salts. The aqueous phase was extracted twice with EtOAc, and the combined the organics were washed with water and brine, dried over MgSO4, concentrated, and chromatographed to provide 250 mg of 2-(4-benzyl-piperazin-1-yl)-3-methyl-3H-imidazole-4-carbaldehyde and 2-(4-benzyl-piperazin-1-yl)-1-methyl-1H-imidazole-4-carbaldehyde as a 1:1 mixture of isomers.

1. temperatureThe mixture was heated
2. temperatureat reflux overnight
3. temperaturethe mixture was heated
4. temperatureto reflux overnight
5. temperatureThe mixture was cooled
6. concentrationconcentrated
7. dissolutiondissolved in EtOAc with a small amount of water
8. dissolutionto dissolve salts
9. extractionThe aqueous phase was extracted twice with EtOAc
10. washorganics were washed with water and brine
11. dry with materialdried over MgSO4
12. concentrationconcentrated
13. customchromatographed