Methyl iodide → 4-Benzyl-1-methylpiperazin-2-one

HRID 1981615Notes

Reaction equation

HRID 1981615 reaction equation
[H-].[Na+].[C:3]1([CH2:9][N:10]2[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17]I>C1COCC1>[CH3:17][N:13]1[CH2:14][CH2:15][N:10]([CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:11][C:12]1=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 114581771-Benzyl-3-oxopiperazine

Product 1

HCID 135204104-Benzyl-1-methylpiperazin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (50% in oil, 10.4 g., 0.22 mole) is added to a stirred solution of 4-(phenylmethyl)piperazinone (Example 45, 38.0 g., 0.20 mole) in THF (2.0 l.). After 1 hour methyl iodide (80.0 g., 0.75 mole) is added and the reaction solution is refluxed for 2.5 hours. The THF is removed under reduced pressure and the residual oil is partitioned between chloroform and water. Evaporation of the chloroform gives an oil which is chromatographed on silica gel to give the title compound, which is converted to the p-TSA salt, m.p. 138°-140°.

Workup

  1. temperaturethe reaction solution is refluxed for 2.5 hours
  2. customThe THF is removed under reduced pressure
  3. customthe residual oil is partitioned between chloroform and water
  4. customEvaporation of the chloroform
  5. customgives an oil which
  6. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-d780ef1e05b64fa6b19d5b87947c2da8
Source dataset
uspto-grants-1986_06
Patent number
US04593098

Reaction notes

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