Methyl iodide → 3,3,4-Trimethylpiperazin-2-one

HRID 1516798Notes

Reaction equation

HRID 1516798 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8].[C:10](=O)([O-])[O-].[K+].[K+].CI>COCCOC>[CH3:1][C:2]1([CH3:9])[N:7]([CH3:10])[CH2:6][CH2:5][NH:4][C:3]1=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2111572-Piperazinone, 3,3-dimethyl-

Product 1

HCID 203101823,3,4-Trimethylpiperazin-2-oneYield 73.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
42.5 °C

Procedure

3,3-dimethylpiperazin-2-one (50 grams) is suspended in 1,2-dimethoxyethane (DME) (150 ml) and potassium carbonate (70 grams) is added. Methyl iodide (66.4 grams) is added during half an hour, while the mixture is cooled slightly, allowing the temperature to reach 50° C. The mixture is stirred 9 hours at an oil bath at 40-45° C., and a sample is withdrawn for NMR, which indicates, that there is still 8% starting material left (singal at 2.8 ppm). More methyl iodide is added (4.6 grams), and the mixture is stirred for another 2½ hour at 40° C., and a new NMR sample shows full conversion. The mixture is filtered, and the filter cake is washed with DME. The filtrate is evaporated to dryness giving 41 grams of the title compound. NMR complies with the structure.

Workup

  1. temperatureis cooled slightly
  2. customto reach 50° C
  3. customa sample is withdrawn for NMR, which
  4. waitleft (singal at 2.8 ppm)
  5. additionMore methyl iodide is added (4.6 grams)
  6. stirringthe mixture is stirred for another 2½ hour at 40° C.
  7. filtrationThe mixture is filtered
  8. washthe filter cake is washed with DME
  9. customThe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-fa5225fca992492f9b30e16ae2e95132
Source dataset
uspto-grants-2012_07
Patent number
US08227607B2

Reaction notes

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