Ethanol → Ethyl Piperazine-2-carboxylate

HRID 1872889Notes

Reaction equation

HRID 1872889 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:9]([OH:11])=[O:10].[CH2:12](O)[CH3:13].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:12]([O:10][C:9]([CH:4]1[CH2:5][NH:6][CH2:7][CH2:8][NH:3]1)=[O:11])[CH3:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2723757Piperazine-2-carboxylic acid dihydrochloride

Product 1

HCID 10633257Ethyl Piperazine-2-carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-piperazinecarboxylic acid dihydrochloride (5.06 g, 0.025 mol), ethanol (100 ml) and concentrated sulphuric acid (6.0 ml) was heated at reflux temperature for 6 days. Toluene (10 ml) was added, and the resulting mixture was concentrated in vacuo to 213 of its original volume. Cold, saturated aqueous potassium carbonate (80 ml) was added and the mixture was extracted with toluene (3×100 ml). The combined organic extracts were washed with brine (30 ml), dried (MgSO4) and concentrated in vacuc, affording 1.0 g (26%) of 2-piperazinecarboxylic acid ethyl ester as an oil. The oil crystallised upon standing at room temperature.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 6 days
  3. concentrationthe resulting mixture was concentrated in vacuo to 213 of its original volume
  4. additionCold, saturated aqueous potassium carbonate (80 ml) was added
  5. extractionthe mixture was extracted with toluene (3×100 ml)
  6. washThe combined organic extracts were washed with brine (30 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuc

Sources & evidence

ORD record
ord-afa5a7ad2bfd489b9ee539e492dbc093
Source dataset
uspto-grants-2000_08
Patent number
US06110913

Reaction notes

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