N-methoxymethyl-N-methylpyrrolidinium chloride → HCID 86639053, compound
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]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- customThe mixture was reacted at room temperature for 9 hours
- filtrationfiltered
- concentrationThe filtrate was concentrated at reduced pressure
- customdried in vacuum
- additionTo the resulting product was added 5000 ml of dehydrated ethanol (reagent, Kanto Kagaku Co., Ltd.)
- temperaturecooled to −25° C
- filtrationThe mixture was filtered
- concentrationconcentrated
- customdried in vacuum
- customThe residue was purified through alumina column (ICN Biomedicals. GmbH, ICN Alumina N, Act.1/eluent acetonitrile)
- concentrationThe eluate was concentrated
- customdried in vacuum
Sources & evidence
- ORD record
- ord-52819292c97748b3be7c7cfbf89b9839
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07854854B2
Reaction notes
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