Piperazine → HCID 57808432, compound

HRID 2105175Notes

Reaction equation

HRID 2105175 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([C@@H:11]1[N:16]([CH3:17])[C:15](=O)[CH2:14][NH:13][C:12]1=O)([CH2:9][CH3:10])[CH3:8].N1CCNCC1>C1COCC1.C(OCC)C>[CH:7]([C@H:11]1[CH2:12][NH:13][CH2:14][CH2:15][N:16]1[CH3:17])([CH2:9][CH3:10])[CH3:8]

Participants

6

Reactant 3

HCID 4837PiperazineHCID 21226445Aluminium lithium hydrideHCID 57808434HCID 57808434, compound

Product 1

HCID 57808432HCID 57808432, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

An oven-dried, nitrogen purged flask was charged with 124 mg LiAlH4 (3.26 mmol) and suspended in 2.0 mL anhydrous THF. Diketopiperazine 11 (200 mg, 1.09 mmol) was added dropwise as a solution in 7.0 mL anhydrous THF. The reaction was stirred at room temperature for 1.5 hours, followed by heating at 40° C. for 5 hours. The reaction was allowed to cool to room temperature, diluted with ca. 10 mL diethyl ether, quenched with sequential addition of 60 μL H2O, 120 μL 10% NaOH, 180 μL H2O, and the resulting aluminum salts filtered off. The organic solution was dried over MgSO4 and evaporated to dryness under reduced pressure to yield 140 mg (82% yield) of product piperazine as a slightly brown oil which was used immediately without further purification. MS (ESI-TOF) MH+ expected: 157.1699, found: 157.1703.

Workup

  1. temperatureby heating at 40° C. for 5 hours
  2. temperatureto cool to room temperature
  3. customquenched with sequential addition of 60 μL H2O, 120 μL 10% NaOH, 180 μL H2O
  4. filtrationthe resulting aluminum salts filtered off
  5. dry with materialThe organic solution was dried over MgSO4
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-548f9db86684459eb0340c99fc89dc3b
Source dataset
uspto-grants-2009_08
Patent number
US07579350B2

Reaction notes

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