Chloroform → 1-(2-Methoxyethyl)-1-methylpyrrolidin-1-ium bromide

Temperature

65 °C

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.

1. temperatureThe mixture was heated to a gradually raised temperature
2. customto terminate
3. customthe reaction
4. temperatureThe reaction mixture was cooled to room temperature
5. filtrationthe resulting solids were filtered off under a nitrogen stream
6. washThe filter cake was washed with 70 g of toluene
7. dry with materialdried in a vacuum (giving 78.99 g of a brown solid product)
8. customThe solid product obtained
9. stirringthe suspension was stirred at room temperature
10. washby washing
11. stirringwith stirring at room temperature
12. filtrationfiltration under a nitrogen stream
13. custom) The product was dried in a vacuum
14. customto result in a yield of 62.64 g
15. addition6.00 g of activated carbon (Carboraffin, product of Takeda Pharmaceutical Co., Ltd.) was added to the solution
16. stirringthe mixture was stirred at 90 to 95° C. for 12 hours
17. temperatureThe mixture was cooled to room temperature
18. customthe activated carbon was separated off by filtration
19. concentrationThe filtrate was concentrated in a vacuum
20. customby drying in a vacuum
21. customto result in a yield of 58.34 g
22. temperaturewith heating for recrystallization
23. customThe resulting white solids obtained
24. filtrationwere filtered off in a nitrogen stream
25. washwashed with 50 g of acetone
26. customdried in a vacuum

ORD record

ord-d6ded63c8f47445ea9e0b9b5afc2bca6

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834197B2