反应详情

A solution/suspension of 4-[(methanesufonyl)amino]benzoic acid (1.62 g, 7.5 mmol) in anhydrous tetrahydrofuran (6 ml) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.38 g, 8.5 mmol), stirred for 45 minutes, and degassed under a stream of nitrogen over 15 minutes. A solution of 3-hydroxy-1-azabicyclo[2.2.2]oct-3-ylmethanamine (1.56 g, 10 mmol) in anhydrous tetrahydrofuran (6 mL) was added, and the mixture soon became cloudy. After 18 hours at room temperature and 90 minutes at 50° C. the mixture was concentrated in vacuo and the residue was triturated from acetonitrile. The foamy solid thus obtained was filtered through alumina (eluted with 1:1 methanol/tetrahydrofuran) and the filtrate was concentrated in vacuo and recrystallized from 2-propanol/ether to afford 1.92 g (71%) of the title compound as a hygroscopic voluminous colorless solid (water soluble); mp 123°-125° C. (foam).

1. customdegassed under a stream of nitrogen over 15 minutes
2. waitAfter 18 hours at room temperature
3. concentration90 minutes at 50° C. the mixture was concentrated in vacuo
4. customthe residue was triturated from acetonitrile
5. customThe foamy solid thus obtained
6. filtrationwas filtered through alumina (eluted with 1:1 methanol/tetrahydrofuran)
7. concentrationthe filtrate was concentrated in vacuo
8. customrecrystallized from 2-propanol/ether