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

HRID 249875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249875
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 17750461(3S)-1-Benzyl-3-ethylpiperazineAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0c5ce07f52754868814d88381a2f7f6b
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863271B2

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