反应详情

A solution of N-(2-carbamoylethyl)-4-cyanopyridinium chloride (2.1 g) in water (5 ml) was added dropwise to a stirred mixture of 4-hydroxypropylpiperidine (2.4 g), water (10 ml) and 2.5M sodium hydroxide solution (4.6 ml) cooled in an ice-bath. The mixture was stirred at 0°-5° C. for 1 hour. 2.5M sodium hydroxide solution (7 ml) was added and the mixture heated at reflux for 3 hours. The mixture was cooled in an ice-bath and gummy solid separated out. The aqueous layer was decanted off and the gummy solid dissolved in dichloromethane (75 ml). The solution was washed with saturated sodium chloride solution (10 ml) and dried (MgSO4). The solvent was removed by evaporation to give a gummy solid (880 mg) which on trituration with ether gave a solid; NMR(d6DMSO): 1.0-1.35(m,4H), 1.35-1.6(m,3H), 1.7(dd,2H), 2.70-2.88(dt,2H), 3.38(t,2H), 3.89(brd,2H), 4.35(brs,1H), 6.78(d,2H), 8.1(d,2H); mass spectrum(CI+): 221(M+H)+.

1. temperaturecooled in an ice-bath
2. temperaturethe mixture heated
3. temperatureat reflux for 3 hours
4. temperatureThe mixture was cooled in an ice-bath
5. customgummy solid separated out
6. customThe aqueous layer was decanted off
7. dissolutionthe gummy solid dissolved in dichloromethane (75 ml)
8. washThe solution was washed with saturated sodium chloride solution (10 ml)
9. dry with materialdried (MgSO4)
10. customThe solvent was removed by evaporation