Hydrochloric Acid → 3-ethylhexahydro-1-methyl-3-(3-oxo-1-cyclohexen-1-yl)-2H-azepin-2-one

HRID 2049185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2049185
C([Mg]Br)(C)C.[CH2:6]([CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]1=[O:16])[CH3:7].C(NC(C)C)(C)C.C[O:25][C:26]1[CH2:31][CH2:30][CH2:29][C:28](=O)[CH:27]=1.Cl>CCOCC.C1COCC1>[CH2:6]([C:8]1([C:28]2[CH2:29][CH2:30][CH2:31][C:26](=[O:25])[CH:27]=2)[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]1=[O:16])[CH3:7]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 855973-Methoxycyclohex-2-en-1-oneHCID 1084053-Ethylhexahydro-1-methyl-2H-azepin-2-oneHCID 178418365HCID 178418365, Verbindung

Produkt 1

HCID 119705853-ethylhexahydro-1-methyl-3-(3-oxo-1-cyclohexen-1-yl)-2H-azepin-2-oneAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 2 molar solution of isopropylmagnesium bromide in ether (70 ml) was treated with 3-ethyl-hexahydro-1-methyl-2H-azepin-2-one (21.7 g, Aust. J. Chem. 1976, 29 2651) in THF (20 ml) and the mixture treated dropwise with diisopropylamine (19.6 ml) (exothermic). The reaction mixture was stirred for 2 hours then treated dropwise with 3-methoxy-2-cyclohexenone (12.6 g) in THF (20 ml). After stirring for 2 hours the reaction mixture was poured onto cold 2 N HCl (250 ml). After 10 minutes the mixture was extracted with dichloromethane (2×300 ml), the combined organic phases washed with saturated aqueous NaHCO3 solution and dried (MgSO4). Removal of the solvents under reduced pressure followed by distillation gave the title compound as a viscous oil (Bpt 155°-160° C./0.1 mm) (13 g). Redistillation (154°-158° C./0.07 mm) gave analytically pure material.

Aufarbeitung

  1. stirringAfter stirring for 2 hours the reaction mixture
  2. extractionAfter 10 minutes the mixture was extracted with dichloromethane (2×300 ml)
  3. washthe combined organic phases washed with saturated aqueous NaHCO3 solution
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvents under reduced pressure
  6. distillationfollowed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-7901c479bb2240ad902c429e2149e98e
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04197239

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