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

HRID 1800867Notes

Reaction equation

HRID 1800867 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[Br:7][CH2:8][CH2:9][O:10][CH3:11]>CC(C)=O>[Br-:7].[CH3:11][O:10][CH2:9][CH2:8][N+:2]1([CH3:1])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 84541-MethylpyrrolidineHCID 809722-Bromoethyl methyl ether

Product 1

HCID 667773211-(2-Methoxyethyl)-1-methylpyrrolidin-1-ium bromideYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-methylpyrrolidine (9.11 g, 0.1 mol), 1-bromo-2-methoxyethane (15.0 g, 0.107 mol) and anhydrous acetone (40 cm3) was refluxed for 24 h. After evaporation under reduced pressure, the yellow solid was washed with diethylether. 1-(2-methoxyethyl)-1-methylpyrrolidinium bromide was obtained as white solid in ca. 70% yield. δH (500.13 MHz, CDCl3) 3.95 (2H, m), 3.85 (6H, m), 3.40 (3H, s), 3.23 (3H, s), 2.29 (4H, m).

Workup

  1. temperaturewas refluxed for 24 h
  2. customAfter evaporation under reduced pressure
  3. washthe yellow solid was washed with diethylether

Sources & evidence

ORD record
ord-c650696116b0404487705eb823788f26
Source dataset
uspto-grants-2013_01
Patent number
US08345407B2

Reaction notes

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