反应详情

To a solution of 18.0 g (0.76 mmol) of N-[4-(aminomethyl)phenyl]methanesulfonamide hydrochloride in 200 mL of methanol, add a solution of 3.04 g of sodium hydroxide in 10 mL of water. Stir for fifteen minutes. Add 11.14 g (0.076 mmol) of 1,2-epoxy-3-phenoxy propane and reflux for 4.5 h. Monitor the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1). Remove the solvent in vacuo. Chromatograph the oil on 800 g of silica gel using a mixture of methylene chloride:methanol:triethylamine (97:2:1) initially and changing to methylene chloride, methanol, triethylamine (95:4:1). Combine the fractions containing product and remove the solvent in vacuo. Dissolve the product in methanol and add a solution of hydrogen chloride in methanol. Remove the solvent in vacuo. Recrystallize the salt from acetonitrile:methanol to obtain the title compound.

1. temperaturereflux for 4.5 h
2. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1)
3. customRemove the solvent in vacuo
4. additionChromatograph the oil on 800 g of silica gel using a mixture of methylene chloride:methanol:triethylamine (97:2:1) initially
5. additionCombine the fractions containing product
6. customremove the solvent in vacuo
7. dissolutionDissolve the product in methanol
8. additionadd a solution of hydrogen chloride in methanol
9. customRemove the solvent in vacuo
10. customRecrystallize the salt from acetonitrile