1-Benzyl-(3R)-methylpiperazine-2-one → 1-Benzyl-3-methylpiperazine

HRID 234283

Reaktionsgleichung

Reaktionsgleichung von HRID 234283
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH3:14])[C:9]1=O)[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[CH2:13][CH2:12][NH:11][CH:10]([CH3:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 100131621-Benzyl-(3R)-methylpiperazine-2-oneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 27275201-Benzyl-3-methylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1-benzyl-3R-methylpiperazine-2-one (XX, 4.36 g), lithium aluminum hydride (LAH, 2.33 g) and THF (125 ml) is heated at reflux for 16 hr. After cooling to 20°-25°, the mixture is quenched slowly with water (2.3 ml), sodium hydroxide (10%, 3.5 ml) and water (5.7 ml). The residue is diluted with ether (100 ml) and is stirred for 1 hr. The solids are filtered and washed successively with ether, methylene chloride and ether. The combined filtrates are dried over potassium carbonate, filtered and concentrated to give 1-benzyl-(3R)-methylpiperazine (XXI), sufficiently pure to be carried on crude, NMR (CDCl3) 7.2-7.4, 3.49, 2.7-3.0, 1.95-2.1, 166, 1.3-1.7 and 1.01 δ.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 16 hr
  3. temperatureAfter cooling to 20°-25°
  4. customthe mixture is quenched slowly with water (2.3 ml), sodium hydroxide (10%, 3.5 ml) and water (5.7 ml)
  5. additionThe residue is diluted with ether (100 ml)
  6. filtrationThe solids are filtered
  7. washwashed successively with ether, methylene chloride and ether
  8. dry with materialThe combined filtrates are dried over potassium carbonate
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2398a8523c694a7981b6f368416efd52
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594140

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