HCID 14278861, compound → 2-Phenylpiperazine

HRID 737084Notes

Reaction equation

HRID 737084 reaction equation
[C:1]1([CH:7]2[NH:12][C:11](=O)[CH2:10][NH:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]1([CH:7]2[CH2:8][NH:9][CH2:10][CH2:11][NH:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14278861HCID 14278861, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 2506732-PhenylpiperazineYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.3 g of 3-phenyl-piperazine-2,5-dione were suspended in anhydrous THF under nitrogen and cooled in an ice-bath. 4 equiv. of lithium aluminium hydride were added. The reaction was stirred at 0° C. for 0.5 h, and then heated to reflux overnight. The reaction was quenched by the subsequent addition of 1 mL/gLiAlH4 of water, 1 mL/gLiAlH4 of 5% aqueous Sodium hydroxide solution and 3 mL/gLiAlH4 of water. The resulting solid were separated by filtration through Celite and rinsed with ethyl acetate. The filtrate was concentrated in vacuo to afford 2 g of 2-phenylpiperazine as brown oil. ES MS (+) m/z 163

Workup

  1. temperaturecooled in an ice-bath
  2. temperatureheated
  3. temperatureto reflux overnight
  4. customThe reaction was quenched by the subsequent addition of 1 mL/gLiAlH4 of water, 1 mL/gLiAlH4 of 5% aqueous Sodium hydroxide solution and 3 mL/gLiAlH4 of water
  5. customThe resulting solid were separated by filtration through Celite
  6. washrinsed with ethyl acetate
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1576c33c250d45e68eed15554173af48
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

Loading…