Methyl iodide → 2-[Acetyl(2,2-diethoxyethyl)amino]-1-methylpyridin-1-ium iodide

HRID 839616Notes

Reaction equation

HRID 839616 reaction equation
[CH2:1]([O:3][CH:4]([O:16][CH2:17][CH3:18])[CH2:5][N:6]([C:13](=[O:15])[CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].[CH3:19][I:20]>C(O)C>[I-:20].[CH3:19][N+:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N:6]([C:13](=[O:15])[CH3:14])[CH2:5][CH:4]([O:16][CH2:17][CH3:18])[O:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 20323729HCID 20323729, compound

Product 1

HCID 203237172-[Acetyl(2,2-diethoxyethyl)amino]-1-methylpyridin-1-ium iodideYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-acetyl-N-(2-pyridyl)-aminoacetaldehyde diethyl acetal (6.0 g.), methyl iodide (25 g.) and ethanol (30 ml.) was heated for 15 hours at 60° C in a sealed tube. The reaction mixture was concentrated and water was added to the residual oil. The mixture was washed twice with ether and the aqueous layer was concentrated under reduced pressure to give oil of 1-methyl-2-[N-acetyl-N-(2,2-diethoxyethyl)-amino]-pyridinium iodide (9.0 g.).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residual oil
  3. washThe mixture was washed twice with ether
  4. concentrationthe aqueous layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e73f7b8b5a2407cbc17f05f6a155811
Source dataset
uspto-grants-1978_06
Patent number
US04096263

Reaction notes

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