1-Methylpyrrolidine → HCID 22020309, compound

HRID 1296813Notes

Reaction equation

HRID 1296813 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[O:7](C)[S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9]>CCCCCC>[F:12][C:11]([F:14])([F:13])[S:8]([O-:10])(=[O:9])=[O:7].[CH3:1][N+:2]1([CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 84541-MethylpyrrolidineHCID 9526Methyl triflate

Product 1

HCID 22020309HCID 22020309, compoundYield 198.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
72.5 °C

Procedure

141.13 g (1.657 mol) of 1-methylpyrrolidine in 800 ml of dry hexane are introduced into a round-bottomed flask fitted with a reflux condenser. 272 g (1.657 mol) of methyl triflate are added over the course of 45 minutes with constant stirring and cooling with the aid of an ice bath. The ice bath is then replaced by an oil bath, and the reaction mixture is refluxed for 15 minutes (oil-bath temperature 70-75° C.). After cooling to room temperature, the white precipitate is filtered off, washed twice with 100 ml of hexane and dried at 110° C. under a 30-100 Pa vacuum for three hours, giving 409 g (yield: 99.1%) of 1,1-dimethylpyrrolidinium trifluoromethanesulfonate as a white solid.

Workup

  1. customfitted with a reflux condenser
  2. temperaturecooling with the aid of an ice bath
  3. temperatureAfter cooling to room temperature
  4. filtrationthe white precipitate is filtered off
  5. washwashed twice with 100 ml of hexane
  6. customdried at 110° C. under a 30-100 Pa vacuum for three hours

Sources & evidence

ORD record
ord-345f4aa5fd1d436a9c0134a07a89a421
Source dataset
uspto-grants-2007_07
Patent number
US07247740B2

Reaction notes

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