Ethyl Glycolate → 2-Hydroxy-1-(4-methylpiperazin-1-yl)ethan-1-one

HRID 1396616Notes

Reaction equation

HRID 1396616 reaction equation
[OH:1][CH2:2][C:3]([O:5]CC)=O.[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>O1CCOCC1>[OH:1][CH2:2][C:3]([N:12]1[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]1)=[O:5]

Participants

4

Reactant 2

HCID 12184Ethyl GlycolateHCID 531671-Methylpiperazine

Product 1

HCID 150689652-Hydroxy-1-(4-methylpiperazin-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

2-Hydroxy-1-(4-methyl piperazin-1-yl)ethanone was prepared according to the following procedure: Ethyl 2-hydroxyacetate (6.85 g, 65.8 mmol, 1.0 eq) and 1-methylpiperazine (5.26 g, 52.6 mmol, 0.8 eq) were dissolved in 1,4-dioxane (10 mL) in a sealed tube and the mixture was stirred at 120° C. overnight. The mixture was allowed to cool to RT and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (2% MeOH-DCM) to afford the product 2-hydroxy-1-(4-methyl piperazin-1-yl)ethanone.

Workup

  1. custom2-Hydroxy-1-(4-methyl piperazin-1-yl)ethanone was prepared
  2. temperatureto cool to RT
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (2% MeOH-DCM)

Sources & evidence

ORD record
ord-83ff8808f45c474c9da821a6e31da501
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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