反应详情

温度

0 °C

Methanesulfonyl chloride (0.43 mL, 5.47 mmol) was added to a solution of 2-(4-bromophenyl)-ethanol (1.0 g, 4.97 mmol) and triethylamine (0.84 mL, 5.96 mmol) in DCM (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes then at ambient temperature for 2 h. The reaction mixture was partitioned between water and DCM and the organic phase was dried over sodium sulfate, filtered and evaporated to give a colourless oil. The resultant residue was dissolved in acetonitrile (10 mL), piperidine (0.491 mL, 4.97 mmol) and potassium carbonate (0.823 g, 5.96 mmol) were added and the reaction mixture was heated at 70° C. for 2.5 h. The reaction mixture was allowed to cool to ambient temperature then partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate, filtered and evaporated and the resultant residue dissolved in methanol and loaded onto a 10 g SCX-2 cartridge. The column was washed with methanol then eluted with 2N ammonia in methanol and the basic fractions were evaporated to afford the title compound (1.27 g, 95%) as a colourless oil. 1H NMR (CDCl3, 300 MHz): 7.41-7.36 (m, 2H), 7.10-7.04 (m, 2H), 2.79-2.71 (m, 2H), 2.54-2.40 (m, 6H), 1.66-1.56 (m, 4H), 1.50-1.40 (m, 2H).

1. waitat ambient temperature for 2 h
2. customThe reaction mixture was partitioned between water and DCM
3. dry with materialthe organic phase was dried over sodium sulfate
4. filtrationfiltered
5. customevaporated
6. customto give a colourless oil
7. temperaturethe reaction mixture was heated at 70° C. for 2.5 h
8. temperatureto cool to ambient temperature
9. customthen partitioned between ethyl acetate and water
10. dry with materialThe organic phase was dried over sodium sulfate
11. filtrationfiltered
12. customevaporated
13. dissolutionthe resultant residue dissolved in methanol
14. washThe column was washed with methanol
15. washthen eluted with 2N ammonia in methanol
16. customthe basic fractions were evaporated