反应详情

Into a mixture comprising 7.30 g of sodium borohydride, 6.00 g of 4-chlorobenzamide and 100 ml of 1,4-dioxane, a mixed solution of 11.58 g of acetic acid and 30 ml of 1,4-dioxane, was dropwise added under stirring and cooling with ice over a period of 30 minutes. After the dropwise addition, the reaction mixture was refluxed under stirring for two hours. After cooling, ice pieces were gradually added to decompose the excess reducing agent, and the solvent was distilled off under reduced pressure Then, the residue was extracted with chloroform. The extract was washed with a saturated sodium chloride aqueous solution, and dried over sodium sulfate, and then the solvent was distilled off to a concentration of about 80 ml. The concentrated solution was cooled with ice, and 10 ml of a dioxane solution of 6N HCl was dropwise added thereto The precipitated solid substance was treated with methanol-ether to obtain 3.16 g of the above identified compound as a colorless powder The NMR spectrum of the free amine is as follows:

1. temperaturecooling with ice over a period of 30 minutes
2. additionAfter the dropwise addition
3. temperaturethe reaction mixture was refluxed
4. stirringunder stirring for two hours
5. temperatureAfter cooling
6. additionice pieces were gradually added
7. distillationthe solvent was distilled off under reduced pressure
8. extractionthe residue was extracted with chloroform
9. washThe extract was washed with a saturated sodium chloride aqueous solution
10. dry with materialdried over sodium sulfate
11. distillationthe solvent was distilled off to a concentration of about 80 ml
12. temperatureThe concentrated solution was cooled with ice, and 10 ml of a dioxane solution of 6N HCl
13. additionwas dropwise added
14. additionThe precipitated solid substance was treated with methanol-ether
15. customto obtain 3.16 g of the