Aluminium lithium hydride → (3S)-1-Benzyl-3-ethylpiperazine

HRID 249875Notes

Reaction equation

HRID 249875 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH3:21])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH3:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 45095306(S)-1-benzyl-3-ethylpiperazine-2-one

Product 1

HCID 17750461(3S)-1-Benzyl-3-ethylpiperazineYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

LiAlH4 (1 M solution in THF, 11 mL, 11.0 mmol) was added drop wise to solution of (S)-1-benzyl-3-ethylpiperazine-2-one (0.8 g, 3.66 mmol) in THF (30 mL) at 0° C. The reaction mixture was stirred at 65° C. for 17 h, then cooled 0° C. and quenched sequentially with H2O (0.7 mL), 10% NaOH (1 mL) and H2O (1.5 mL). Diethylether (100 mL) was added to the reaction mixture, and stirring was continued for 1.5 h. The solid was filtered off, the filtrate was concentrated and dried in vacuum to afford (S)-1-benzyl-3-ethylpiperazine (0.67 g, 87%) as an oily solid. 1H NMR and MS consistent.

Workup

  1. temperaturecooled 0° C.
  2. customquenched sequentially with H2O (0.7 mL), 10% NaOH (1 mL) and H2O (1.5 mL)
  3. additionDiethylether (100 mL) was added to the reaction mixture
  4. stirringstirring
  5. waitwas continued for 1.5 h
  6. filtrationThe solid was filtered off
  7. concentrationthe filtrate was concentrated
  8. customdried in vacuum

Sources & evidence

ORD record
ord-0c5ce07f52754868814d88381a2f7f6b
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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