2-Methylpiperazine → HCID 263198, compound

HRID 1060204Notes

Reaction equation

HRID 1060204 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[CH3:8][C:9]1[O:15]C(C)(C)[O:13][C:11](=O)[CH:10]=1>C1(C)C(C)=CC=CC=1>[C:11]([N:3]1[CH2:4][CH2:5][N:6]([C:11](=[O:13])[CH2:10][C:9]([CH3:8])=[O:15])[CH2:7][CH:2]1[CH3:1])(=[O:13])[CH2:10][C:9]([CH3:8])=[O:15]

Participants

4

Reactant 2

HCID 660572-MethylpiperazineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 263198HCID 263198, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
115 °C

Procedure

To 2-methylpiperazine (81.90 g, 0.819 mol) in xylene (525 ml) at 133° C. was added with stirring 2,2,6-trimethyl-1,3-dioxen-4-one (232.48 g, 1.637 mol) in xylene (525 ml) over 10 minutes, during which the temperature decreased to 100° C. After heating to 115° C over 5 minutes vigorous effervescence commenced, and after heating to 124° C. over another 5 minutes distillation of acetone (through a Vigreux column) also commenced. Pot temperature was increased to 139° C. over a further 30 minutes, with collection of acetone distillate. After cooling to 20° C. overnight, supernatant liquid was separated from deposited syrup, which was dissolved in dichloromethane. Removal of solvent from combined solutions and drying (92° C./100 Pa) gave N,N′-bis(acetoacetyl)-2-methylpiperazine (BAAMPZ) as a viscous syrup (216.66 g, 99%), identified by 1H-NMR, 13C-NMR, FT-IR and Raman spectra.

Workup

  1. customdecreased to 100° C
  2. temperatureafter heating to 124° C. over another 5 minutes
  3. distillationdistillation of acetone (through a Vigreux column)
  4. temperaturePot temperature was increased to 139° C. over a further 30 minutes, with collection of acetone distillate
  5. temperatureAfter cooling to 20° C. overnight
  6. customsupernatant liquid was separated from deposited syrup, which
  7. dissolutionwas dissolved in dichloromethane
  8. customRemoval of solvent from combined solutions
  9. customdrying (92° C./100 Pa)

Sources & evidence

ORD record
ord-1fb205a15a264334bf324261d5bc031f
Source dataset
uspto-grants-2003_02
Patent number
US06521716B1

Reaction notes

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