Trifluoromethanesulfonic acid → N-methoxymethyl-N-methylpyrrolidinium trifluoromethanesulfonate

HRID 254894Notes

Reaction equation

HRID 254894 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][N+:5]1([CH3:10])[CH2:9][CH2:8][CH2:7][CH2:6]1.[F:11][C:12]([F:18])([F:17])[S:13]([OH:16])(=[O:15])=[O:14]>C(Cl)(Cl)Cl>[F:11][C:12]([F:18])([F:17])[S:13]([O-:16])(=[O:15])=[O:14].[CH3:2][O:3][CH2:4][N+:5]1([CH3:10])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 23116042N-methoxymethyl-N-methylpyrrolidinium chloride

Product 1

HCID 86618680N-methoxymethyl-N-methylpyrrolidinium trifluoromethanesulfonateYield 95.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 116 g of dehydrated chloroform (reagent, Wako Pure Chemical Ind. Ltd.) was dissolved 24.3 g of N-methoxymethyl-N-methylpyrrolidinium chloride. To the solution was added dropwise 24.3 g of trifluoromethane sulfonic acid (reagent, Aldrich Corp.) at 5° C. over a period of 1 hour. The mixture was reacted at room temperature for 2 hours with gradual increase of temperature. The reaction mixture was concentrated and dried in a vacuum. The residue was purified through alumina column (ICN Biomedicals. GmbH, ICN Alumina N, Act.1/eluent acetonitrile). The eluate was concentrated and dried in a vacuum to obtain 39.1 g of the desired product (colorless liquid).

Workup

  1. customThe mixture was reacted at room temperature for 2 hours
  2. temperaturewith gradual increase of temperature
  3. concentrationThe reaction mixture was concentrated
  4. customdried in a vacuum
  5. customThe residue was purified through alumina column (ICN Biomedicals. GmbH, ICN Alumina N, Act.1/eluent acetonitrile)
  6. concentrationThe eluate was concentrated
  7. customdried in a vacuum

Sources & evidence

ORD record
ord-0aca38ac87b54e4996621794bc5a5aad
Source dataset
uspto-grants-2011_01
Patent number
US07875732B2

Reaction notes

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