N-methoxymethyl-N-methylpyrrolidinium chloride → HCID 86639053, compound

HRID 2264103Notes

Reaction equation

HRID 2264103 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][N+:5]1([CH3:10])[CH2:9][CH2:8][CH2:7][CH2:6]1>O.[Ag]OC#N>[N-:5]=[C:4]=[O:3].[CH3:2][O:3][CH2:4][N+:5]1([CH3:10])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Conditions

Temperature
5 °C

Procedure

In 325 g of water was dissolved 55.5 g of N-methoxymethyl-N-methylpyrrolidinium chloride and thereto was added 51.0 g of silver cyanate(reagent, Aldrich Corp.). The mixture was reacted at room temperature for 9 hours, cooled to 5° C. and filtered. The filtrate was concentrated at reduced pressure and dried in vacuum. To the resulting product was added 5000 ml of dehydrated ethanol (reagent, Kanto Kagaku Co., Ltd.) and cooled to −25° C. The mixture was filtered, concentrated and dried in 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 vacuum to obtain 43.6 g of the desired product (colorless liquid). The product was checked for 1H-NMR, electrical conductivity and voltage resistance as in Example 1.

Workup

  1. customThe mixture was reacted at room temperature for 9 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated at reduced pressure
  4. customdried in vacuum
  5. additionTo the resulting product was added 5000 ml of dehydrated ethanol (reagent, Kanto Kagaku Co., Ltd.)
  6. temperaturecooled to −25° C
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated
  9. customdried in vacuum
  10. customThe residue was purified through alumina column (ICN Biomedicals. GmbH, ICN Alumina N, Act.1/eluent acetonitrile)
  11. concentrationThe eluate was concentrated
  12. customdried in vacuum

Sources & evidence

ORD record
ord-52819292c97748b3be7c7cfbf89b9839
Source dataset
uspto-grants-2010_12
Patent number
US07854854B2

Reaction notes

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