Water → 2-Benzylpiperazine

HRID 1986901Notes

Reaction equation

HRID 1986901 reaction equation
[CH2:1]([CH:8]1[NH:13][C:12](=O)[CH2:11][NH:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH2:1]([CH:8]1[NH:13][CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1384093-Benzyl-3,6-dihydropyrazine-2,5-diolHCID 21226445Aluminium lithium hydride

Product 1

HCID 5590332-Benzylpiperazine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 3-benzyl-piperazine-2,5-dione (14.98 g, 73 mmol, prepared following generally the procedure of Halpern and Westley, J. Org. Chem. 1968, 33, 864) in dry diethyl ether (500 mL) is added dropwise to a solution of lithium aluminum hydride (400 mL of a 1 M solution in diethyl ether, 400 mmol, 5.4 eq). The suspension is heated at reflux for 23 hours and then cooled to 0° C. Water (70 mL) is then cautiously added and the resulting suspension is warmed to room temperature. After 3 hours the suspension is filtered and the solid washed with diethyl ether (1 L).

Workup

  1. customprepared
  2. temperatureThe suspension is heated
  3. temperatureat reflux for 23 hours
  4. temperaturethe resulting suspension is warmed to room temperature
  5. filtrationAfter 3 hours the suspension is filtered
  6. washthe solid washed with diethyl ether (1 L)

Sources & evidence

ORD record
ord-3418816c359649d9b253d9eb08656144
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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