反应详情

A solution of 1-benzyl-4,4-diethoxy-piperidin-3-ylamine 16 (600 mg, 2.2 mmol), and m-tolyl isothiocyanate (328 mg, 2.2 mmol) in 10 mL chloroform was heated at 60° C. for 2 hr. The solvent was removed in vacuo, and the residue was treated with 10 mL each of 10% hydrochloric acid and dioxane and heated at reflux for 1 h. After removal of the solvent the residue was dissolved in 50 mL ethanol followed by addition of Raney Nickel (ca. 3.0 g). The suspension was heated at reflux for 2 h then allowed to cool to room temperature. The solids were removed by filtration. The solvent was evaporated in vacuo, and the residue was diluted with 10% sodium hydroxide solution and extracted into chloroform. The organic layer was dried over potassium carbonate, filtered and concentrated to provide 500 mg of 5-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 17a as a light brown oil, [M+H]+=304.

1. customThe solvent was removed in vacuo
2. additionthe residue was treated with 10 mL each of 10% hydrochloric acid and dioxane
3. temperatureheated
4. temperatureat reflux for 1 h
5. customAfter removal of the solvent the residue
6. dissolutionwas dissolved in 50 mL ethanol
7. additionfollowed by addition of Raney Nickel (ca. 3.0 g)
8. temperatureThe suspension was heated
9. temperatureat reflux for 2 h
10. customThe solids were removed by filtration
11. customThe solvent was evaporated in vacuo
12. additionthe residue was diluted with 10% sodium hydroxide solution
13. extractionextracted into chloroform
14. dry with materialThe organic layer was dried over potassium carbonate
15. filtrationfiltered
16. concentrationconcentrated