Reaction #470364

ord-143614ae0ca4455dacc462476a3cf9db

Reaction equation

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
COC[N+]1(C)CCCC1.[Cl-]
N-methoxymethyl-N-methylpyrrolidinium chloride
COC[N+]1(C)CCCC1.[Cl-]
N-Methyl-N-Methoxymethylpyrrolidinium Chloride
COC[N+]1(C)CCCC1.COC[N+]1(C)CCCC1.O=C([O-])[O-]
desired product
COC[N+]1(C)CCCC1.COC[N+]1(C)CCCC1.O=C([O-])[O-]
N-Methoxymethyl-N-Methylpyrrolidinium Carbonate

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe mixture was reacted at room temperature for 0.5 hour
  2. 2
    Otherwhereby the reaction was terminated
  3. 3
    ConcentrationThe reaction mixture was concentrated
  4. 4
    Dryingdried in vacuum, and 100 ml of ethyl alcohol
  5. 5
    workup.ADDITIONwas added to the residue
  6. 6
    Otherto remove insoluble sodium chloride
  7. 7
    workup.DISSOLUTIONThe resulting product was dissolved in dichloromethane
  8. 8
    Filtrationthe solution was filtered with a membrane
  9. 9
    Filtrationfilter again
  10. 10
    Concentrationthe filtrate was concentrated in a vacuum
  11. 11
    Otherdried

Procedure

A 1.60 g quantity of sodium carbonate (product of Wako Pure Chemical Ind. Ltd.) was dissolved in 18 g of deionized water, and 5.01 g of N-methoxymethyl-N-methylpyrrolidinium chloride was added to the solution. The mixture was reacted at room temperature for 0.5 hour, whereby the reaction was terminated. The reaction mixture was concentrated and dried in vacuum, and 100 ml of ethyl alcohol was added to the residue to remove insoluble sodium chloride. The resulting product was dissolved in dichloromethane, the solution was filtered with a membrane filter again, and the filtrate was concentrated in a vacuum and dried, giving 5.41 g of the desired product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08366956B2uspto-grants-2013_02