Methyl iodide → 4-Cbz-1-methyl-2-piperazinone

HRID 1436490

Reaktionsgleichung

Reaktionsgleichung von HRID 1436490
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:21]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:21])[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylate

Produkt 1

HCID 586385404-Cbz-1-methyl-2-piperazinoneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve 4-benzyloxycarbonylpiperazin-2-one (2 g, 8.6 mmol) in THF (10 mL). Add sodium hydride (236 mg, 9.4 mmol, 60% dispersion in mineral oil) in one portion and stir at room temperature for 30 min. Add iodomethane (0.8 mL, 13 mmol) and stir at room temperature overnight. Concentrate, add ethyl acetate and wash with water. Separate organic layer, wash with saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with ethyl acetate) to give the title compound as a yellow oil (1.7 g, 82%).

Aufarbeitung

  1. concentrationConcentrate
  2. additionadd ethyl acetate
  3. washwash with water
  4. washSeparate organic layer, wash with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a3975763d88b46c092902f66e2dd8321
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618978B2

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