Sodium Methoxide → 4-Benzoyl-1-(2-phenylethyl)piperazine-2,6-dione

HRID 1248276Notes

Reaction equation

HRID 1248276 reaction equation
[C:1]([N:9]1[CH2:14][C:13](=[O:15])[NH:12][C:11](=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].CS([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=O)=O>CN(C)C=O>[C:1]([N:9]1[CH2:10][C:11](=[O:16])[N:12]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13](=[O:15])[CH2:14]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12424890HCID 12424890, compoundHCID 130638154-Benzoylpiperazine-2,6-dione

Product 1

HCID 130638174-Benzoyl-1-(2-phenylethyl)piperazine-2,6-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

12 g (0.055 mol) of 4-benzoyl-2,6-dioxopiperazine are dissolved in 200 ml of dimethylformamide. 3.5 g (0.065 mol) of sodium methylate are added and the reaction medium is left for 1 hour at ambient temperature. To the reaction medium is added, dropwise and in an inert atmosphere, a solution of 16 g (0.080 mol) of (2-methane-sulphonyl ethyl)-benzene in 50 ml of dimethylformamide and is brought to 70° C. for 5 hours. Evaporation to dryness is carried out under vacuum and the residue is taken up in a mixture of water and dichloromethane. The decanted organic phase is dried over dry sodium sulphate. The evaporation of the solvent leaves an oily residue which is purified by silica column chromatography (elutrient: toluene/ethyl acetate 7/3). In this way, there is obtained the 4-benzoyl-2,6dioxo-1-phenethyl piperazine which, after recrystallisation from a cyclohexane/ethyl acetate mixture, melts at 102° C.

Workup

  1. additionTo the reaction medium is added
  2. customEvaporation to dryness
  3. additionthe residue is taken up in a mixture of water and dichloromethane
  4. dry with materialThe decanted organic phase is dried over dry sodium sulphate
  5. customThe evaporation of the solvent
  6. customleaves an oily residue which
  7. customis purified by silica column chromatography (elutrient: toluene/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-99821c074a8f4e0fa38ccba68ac0c468
Source dataset
uspto-grants-1985_06
Patent number
US04523013

Reaction notes

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