Aluminium lithium hydride → (2R)-2-(4-methoxybenzyl)-4-benzylpiperazine

HRID 1375042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375042
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][C:18](=O)[NH:17][C@H:16]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C@@H:16]2[CH2:15][N:14]([CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:19][CH2:18][NH:17]2)=[CH:27][CH:26]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 54330683(3R)-1-benzyl-3-(4-methoxybenzyl)piperazine-2,5-dione

Produkt 1

HCID 53781111(2R)-2-(4-methoxybenzyl)-4-benzylpiperazineAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, to a suspension of lithium aluminum hydride (0.85 g) in tetrahydrofuran (65 ml) was added (3R)-1-benzyl-3-(4-methoxybenzyl)piperazine-2,5-dione (3.65 g) portionwise under ice-bath cooling. The reaction mixture was refluxed with stirring for one hour. After cooling, it was quenched by sequential addition of water (0.85 ml), 15% aqueous sodium hydroxide (0.85 ml), and water (2.5 ml) and the whole was stirred at room temperature for 30 minutes. The resulting insoluble material was removed by filtration, and the filtrate was added to a mixture of ethyl acetate (50 ml) and brine (70 ml). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure to give (2R)-2-(4-methoxybenzyl)-4-benzylpiperazine (3.51 g) as a syrup.

Aufarbeitung

  1. temperaturecooling
  2. temperatureThe reaction mixture was refluxed
  3. temperatureAfter cooling
  4. customit was quenched by sequential addition of water (0.85 ml), 15% aqueous sodium hydroxide (0.85 ml), and water (2.5 ml)
  5. stirringthe whole was stirred at room temperature for 30 minutes
  6. customThe resulting insoluble material was removed by filtration
  7. additionthe filtrate was added to a mixture of ethyl acetate (50 ml) and brine (70 ml)
  8. customThe organic layer was separated
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b7c2b764800b413daae36ca3c4a52c9a
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166598B2

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