Water → 1-Benzyl-3-ethylpiperazine

HRID 420554Notes

Reaction equation

HRID 420554 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][C:18](=O)[NH:17][CH:16]([CH2:21][CH3:22])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1.[Cl-].[Na+].O.C(OCC)(=O)C>[CH2:7]([N:14]1[CH2:19][CH2:18][NH:17][CH:16]([CH2:21][CH3:22])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 222733891-Benzyl-3-ethylpiperazine-2,5-dione

Product 1

HCID 220365411-Benzyl-3-ethylpiperazine

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of lithium aluminium hydride (0.87 g; 22.9 mmol) in anhydrous THF (20 ml) was added dropwise a solution of 1-benzyl-3-ethylpiperazine-2,5-dion (1.50 g; 6.46 mmol) in anhydrous THF (10 ml) under ice-cooling. After stirring at room temperature for 18 hours, a mixture of water (0.25 ml) and THF (5 ml) and 2N-aqueous sodium hydroxide solution (0.5 ml) were added dropwise sequentially under ice-cooling. The mixture was stirred at room temperature for 1 hour. After filtration of aluminium hydroxide, the filtrate was condensed under reduced pressure. To the residue were added ethyl acetate and brine to separate. The organic layer was dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to give 1-benzyl-3-ethylpiperazine as pale yellow oil (1.29 g; 98%).

Workup

  1. temperaturecooling
  2. additionwere added dropwise sequentially under ice-
  3. temperaturecooling
  4. stirringThe mixture was stirred at room temperature for 1 hour
  5. filtrationAfter filtration of aluminium hydroxide
  6. customcondensed under reduced pressure
  7. customto separate
  8. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cb951f7796534bfdae1d0583b1caa986
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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