反应详情

温度

2.5 °C

To a solution of 2-[3-(3,4-dichlorophenyl)piperidin-3-yl]ethanol (1.92 g, 7.00 mmol) in tetrahydrofuran (100 ml) was added triethylamine (1.50 ml, 10.8 mmol), and the resulting mixture was cooled to 0-5° C. After cooling, a solution of 3,4,5-trimethoxybenzoyl chloride (1.65 g, 7.14 mmol) in tetrahydrofuran (8 ml) was further added dropwise at below 5° C., and the resulting mixture was stirred at 0-5° C. for 4 hours and then evaporated to dryness in vacuo. To the obtained residue, methylene chloride (50 ml), triethylamine (1.50 ml, 10.8 mmol) and 4-dimethylaminopyridine (0.086 g, 0.70 mmol) were added, and the resulting mixture was cooled to 0-5° C. After cooling, a solution of 4-chlorobenzenesulfonyl chloride (1.77 g, 8.39 mmol) in methylene chloride (4 ml) was further added dropwise at below 5° C., and the resulting mixture was stirred at 0-5° C. for 6 hours. After completion of the reaction, water (50 ml) and concentrated hydrochloric acid (2 ml) were added to the reaction mixture, and the resulting mixture was partitioned. The separated organic layer was washed with water (50 ml) and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column and then crystallized from a mixed solvent of ethyl acetate (7.5 ml) and hexane (20.3 ml) under ice-cooling to afford the title compound [3.1 g, yield: 68.9%] as a colorless crystalline solid.

1. temperatureAfter cooling
2. customevaporated to dryness in vacuo
3. temperaturethe resulting mixture was cooled to 0-5° C
4. temperatureAfter cooling
5. stirringthe resulting mixture was stirred at 0-5° C. for 6 hours
6. additionwere added to the reaction mixture
7. customthe resulting mixture was partitioned
8. washThe separated organic layer was washed with water (50 ml)
9. customevaporated in vacuo
10. customThe residue obtained
11. customwas purified by chromatography on a silica gel column
12. customcrystallized from a mixed solvent of ethyl acetate (7.5 ml) and hexane (20.3 ml) under ice-
13. temperaturecooling