Sulfuric acid magnesium salt (1:1) → Tert-butyl 2-(1-methylpiperidin-4-yl)hydrazinecarboxylate

HRID 1530648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530648
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[O-]S([O-])(=O)=O.[Mg+2].[NH:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH2:16]>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:16][NH:15][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 70091tert-Butyl carbazateHCID 740491-Methyl-4-piperidone

Produkt 1

HCID 68313226Tert-butyl 2-(1-methylpiperidin-4-yl)hydrazinecarboxylateAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-methylpiperidin-4-one (3.0 g, 27 mmol) in DCM (60 mL) was added MgSO4 (6.5 g, 54 mmol) and tert-butyl hydrazinecarboxylate (2.9 g, 22 mmol). The reaction mixture was heated to reflux overnight. The solid was filtered off and the filtrate was concentrated. The residue was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:20) to give tert-butyl 2-(1-methylpiperidin-4-yl)hydrazinecarboxylate (3.2 g, 53% yield) as a colorless oil. LCMS (ESI) m/z: 228.3 [M+H+].

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with EtOAc/petroleum ether (1:20)

Quellen und Nachweise

ORD-Eintrag
ord-043f25c0f9a941c89c9ad3c17e94a60a
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090628B2

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