1-Methylpyrrolidine → 1-(Methoxymethyl)-1-methylpyrrolidin-1-ium bromide

HRID 1174035Notes

Reaction equation

HRID 1174035 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:7][O:8][CH2:9][Br:10]>CC(C)=O.O>[Br-:10].[CH3:7][O:8][CH2:9][N+:2]1([CH3:1])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 84541-MethylpyrrolidineHCID 83093Bromomethyl methyl ether

Product 1

HCID 231160401-(Methoxymethyl)-1-methylpyrrolidin-1-ium bromide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

A 17.0 g quantity of N-methylpyrrolidine was dissolved in 160 g of dehydrated acetone (up to 0.1% in water content), followed by nitrogen replacement. To the solution was added dropwise 24.6 g of bromomethyl methyl ether (reagent, product of Tokyo Kasei Co., Ltd.) at 5° C. over a period of 1.5 hours. The mixture was stirred at 5 to not higher than 15° C. for 4 hours to terminate the reaction. The reaction mixture was filtered, and the resulting solids were washed with 160 g of acetone, and dried in a vacuum, affording 30.9 g of the desired product (white solid).

Workup

  1. customto terminate
  2. customthe reaction
  3. filtrationThe reaction mixture was filtered
  4. washthe resulting solids were washed with 160 g of acetone
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-d84364220cfa4c0ea714dd4573354c86
Source dataset
uspto-grants-2010_11
Patent number
US07834197B2

Reaction notes

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