Aluminium lithium hydride → 1-Benzyl-2-methoxymethyl-2-methyl-piperazine

HRID 334083Notes

Reaction equation

HRID 334083 reaction equation
[CH2:1]([N:8]1[C:13]([CH2:15][O:16][CH3:17])([CH3:14])[CH2:12][NH:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][NH:11][CH2:12][C:13]1([CH2:15][O:16][CH3:17])[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866883054-Benzyl-5-methoxymethyl-5-methyl-piperazin-2-one

Product 1

HCID 866883061-Benzyl-2-methoxymethyl-2-methyl-piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 130 mg (0.524 mmol) 4-benzyl-5-methoxymethyl-5-methyl-piperazin-2-one in 5 mL THF was cooled with ice and 780 μL (0.780 mmol) 1M lithium aluminum hydride solution in THF was added dropwise under argon atmosphere. The resultant mixture was stirred 3 h under ice-bath cooling and 2.5 h at Rt. Then the mixture was quenched with saturated aqueous Na2SO4 solution, stirred for 1 h, filtered through Celite, washed with EtOAc and concentrated in vacuo.

Workup

  1. additionwas added dropwise under argon atmosphere
  2. temperaturecooling and 2.5 h at Rt
  3. customThen the mixture was quenched with saturated aqueous Na2SO4 solution
  4. filtrationfiltered through Celite
  5. washwashed with EtOAc
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8c929900fdd49debe060efe755fe0d2
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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