1-Methylpyrrolidine → 1-[2-(2-Methoxyethoxy)ethyl]-1-methylpyrrolidin-1-ium bromide

HRID 1800868Notes

Reaction equation

HRID 1800868 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[Br:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14]>CC(C)=O>[Br-:7].[CH3:14][O:13][CH2:12][CH2:11][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 1235321-Bromo-3,6-dioxaheptane

Product 1

HCID 667775811-[2-(2-Methoxyethoxy)ethyl]-1-methylpyrrolidin-1-ium bromideYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-methylpyrrolidine (9.11 g, 0.1 mol), 1-bromo-2-(2-methoxy-ethoxy)ethane (10.0 g, 0.103 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-(2-methoxyethoxy)ethyl]-1-methylpyrrolidinium bromide was obtained as white solid in ca. 68% yield. δH (500.13 MHz, CDCl3) 3.98 (2H, m), 3.87 (6H, m), 3.68 (2H, m), 3.53 (2H, m), 3.40 (3H, s), 3.33 (3H, s), 2.29 (4H, m).

Workup

  1. customAfter evaporation under reduced pressure
  2. washthe yellow solid was washed with diethylether

Sources & evidence

ORD record
ord-c9056972e1524bbd8fb8f5b65fb72c6a
Source dataset
uspto-grants-2013_01
Patent number
US08345407B2

Reaction notes

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