Sodium Chloride → 1-Acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine

HRID 2248866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2248866
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:11](Cl)[CH:12]=[CH:13][CH3:14].[Mg].[Cl-].[Na+]>CCOCC.O1CCCC1>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([OH:10])([CH:13]([CH3:14])[CH:12]=[CH2:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 11589Crotyl chlorideHCID 122563N-Acetyl-4-piperidoneHCID 5462224Magnesium

Produkt 1

HCID 148520451-Acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1.94 g 1-acetyl-4-piperidone in a mixture of ether (80 ml) and tetrahydrofuran (40 ml), was added dropwise at 10° C. or lower 275 ml of a 0.5M Grignard reagent prepared by the usual way from crotyl chloride and magnesium, and the resulting mixture was stirred overnight at room temperature. To the ice-cooled reaction mixture, was slowly added 100 ml of saturated aqueous solution of sodium chloride, and the layers were separated. The aqueous layer was extracted with chloroform, the two organic solutions were each concentrated, and the combined concentrate was subjected to silica gel column chromatography using, as eluent, a mixed solvent of ethyl acetate/n-hexane (1:1 by volume) containing 3% methanol, giving 16.9 g of 1-acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine as oil.

Aufarbeitung

  1. additionwas added dropwise at 10° C.
  2. customreaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with chloroform
  5. concentrationthe combined concentrate
  6. additiona mixed solvent of ethyl acetate/n-hexane (1:1 by volume) containing 3% methanol

Quellen und Nachweise

ORD-Eintrag
ord-3dd7dd505d9045b28a72a8b85f51f3a3
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05041549

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