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

HRID 2049185노트

반응식

HRID 2049185 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

HCID 119705853-ethylhexahydro-1-methyl-3-(3-oxo-1-cyclohexen-1-yl)-2H-azepin-2-one수율 52.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7901c479bb2240ad902c429e2149e98e
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04197239

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