反応 #470361

反応方程式

chloroform

N-methylpyrrolidine

bromoethyl methyl ether

→

N-methoxyethyl-N-methylpyrrolidinium bromide

収率 41.7%

溶媒

water

acetone

toluene

acetone

反応条件

後処理

1. 1
   温度The mixture was heated to a gradually raised temperature
2. 2
   その他to terminate
3. 3
   その他the reaction
4. 4
   温度The reaction mixture was cooled to room temperature
5. 5
   ろ過the resulting solids were filtered off under a nitrogen stream
6. 6
   洗浄The filter cake was washed with 70 g of toluene
7. 7
   乾燥dried in a vacuum (giving 78.99 g of a brown solid product)
8. 8
   その他The solid product obtained
9. 9
   workup.STIRRINGthe suspension was stirred at room temperature
10. 10
    洗浄by washing
11. 11
    workup.STIRRINGwith stirring at room temperature
12. 12
    ろ過filtration under a nitrogen stream
13. 13
    その他) The product was dried in a vacuum
14. 14
    その他to result in a yield of 62.64 g
15. 15
    workup.ADDITION6.00 g of activated carbon (Carboraffin, product of Takeda Pharmaceutical Co., Ltd.) was added to the solution
16. 16
    workup.STIRRINGthe mixture was stirred at 90 to 95° C. for 12 hours
17. 17
    温度The mixture was cooled to room temperature
18. 18
    その他the activated carbon was separated off by filtration
19. 19
    濃縮The filtrate was concentrated in a vacuum
20. 20
    その他by drying in a vacuum
21. 21
    その他to result in a yield of 58.34 g
22. 22
    温度with heating for recrystallization
23. 23
    その他The resulting white solids obtained
24. 24
    ろ過were filtered off in a nitrogen stream
25. 25
    洗浄washed with 50 g of acetone
26. 26
    その他dried in a vacuum

実験手順

N-methylpyrrolidine (31.10 g, reagent, product of Tokyo Kasei Co., Ltd.) was dissolved in 124.30 g of toluene, followed by replacement with nitrogen. To the solution was added dropwise 61.22 g of bromoethyl methyl ether (reagent, product of Aldrich Corp.) at 27° C. over a period of 1 hour. The mixture was heated to a gradually raised temperature and then stirred at 60 to 70° C. for 37 hours to terminate the reaction. The reaction mixture was cooled to room temperature, and the resulting solids were filtered off under a nitrogen stream. The filter cake was washed with 70 g of toluene and thereafter dried in a vacuum (giving 78.99 g of a brown solid product). The solid product obtained was suspended in 200 g of acetone, and the suspension was stirred at room temperature, followed by washing with stirring at room temperature and filtration under a nitrogen stream. (This procedure was repeated twice.) The product was dried in a vacuum to result in a yield of 62.64 g. The product, which was colored, was dissolved in 131.83 g of water, 6.00 g of activated carbon (Carboraffin, product of Takeda Pharmaceutical Co., Ltd.) was added to the solution, and the mixture was stirred at 90 to 95° C. for 12 hours. The mixture was cooled to room temperature, and the activated carbon was separated off by filtration. The filtrate was concentrated in a vacuum, followed by drying in a vacuum to result in a yield of 58.34 g. The product was dissolved in a solvent mixture of 200.48 g of acetone and 27.22 g of chloroform with heating for recrystallization. The resulting white solids obtained were filtered off in a nitrogen stream, washed with 50 g of acetone and dried in a vacuum, giving 34.10 g of N-methoxyethyl-N-methylpyrrolidinium bromide.

出典