Ethanol → Ethyl Piperazine-2-carboxylate

HRID 1979037Notes

Reaction equation

HRID 1979037 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 ⅔ 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 vacuo, 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
  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 vacuo

Sources & evidence

ORD record
ord-0e2c582639c9426e8aac525fde9b9310
Source dataset
uspto-grants-2001_05
Patent number
US06239148B1

Reaction notes

Loading…