反应详情

To a solution of cycloheptanone (1.12 g, 10 mmol) in 40 ml of ethanol was added a methylamine (2.5 ml of a 33% solution in ethanol) and 220 mg of Pd on C (10%) were added, and the mixture hydrogenated at 50 psi over night. The solids were filtered off and the mixture concentrated under vacuum to give a pale yellow oil. This material and 1.2 ml of triethylamine were dissolved in 10 ml of dichloromethane and a solution of [2,1,3]-benzoxadiazole-5-carbonylchloride (730 mg, 4 mmol) was added slowly. After stirring the mixture for 2 hours, the organic phase was washed with 1N HCl and cone. NaHCO3 solution, dried over magnesium sulfate, and then concentrated under vacuum to give a white solid, after trituration with ether (405 mg, 37%). Mp: 80-81° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.93 (m, 1H); 7.80 (s, 1H); 7.43-7.37 (m, 1H); 4.75-4.60 and 3.70-3.55 (m+m, 1H); 3.01 and 2.87 (s+s, 3H); 2.00-1.20 ppm (m, 12H).

1. additionwere added
2. waitthe mixture hydrogenated at 50 psi over night
3. filtrationThe solids were filtered off
4. concentrationthe mixture concentrated under vacuum
5. customto give a pale yellow oil
6. washthe organic phase was washed with 1N HCl and cone
7. dry with materialNaHCO3 solution, dried over magnesium sulfate
8. concentrationconcentrated under vacuum
9. customto give a white solid