Hydrochloric Acid → 3-ethylhexahydro-1-methyl-3-(3-oxo-1-cyclohexen-1-yl)-2H-azepin-2-one
Reaction equation
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]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- stirringAfter stirring for 2 hours the reaction mixture
- extractionAfter 10 minutes the mixture was extracted with dichloromethane (2×300 ml)
- washthe combined organic phases washed with saturated aqueous NaHCO3 solution
- dry with materialdried (MgSO4)
- customRemoval of the solvents under reduced pressure
- distillationfollowed by distillation
Sources & evidence
- ORD record
- ord-7901c479bb2240ad902c429e2149e98e
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04197239
Reaction notes
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