Hydrochloric Acid → hexahydro-3-(3-oxocyclohexen-1-yl)-2H-azepin-2-one

HRID 2049329Notes

Reaction equation

HRID 2049329 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.C[Si](C)(C)[N:23]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=[O:30].C[O:34][C:35]1[CH2:40][CH2:39][CH2:38][C:37](=O)[CH:36]=1.Cl>CCCCCC.C1COCC1.C(Cl)(Cl)Cl>[O:34]=[C:35]1[CH2:40][CH2:39][CH2:38][C:37]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][NH:23][C:24]2=[O:30])=[CH:36]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 855973-Methoxycyclohex-2-en-1-oneHCID 2724682Lithium diisopropylamideHCID 114239991-Trimethylsilanyl-azepan-2-oneHCID 178418339Butyllithium

Product 1

HCID 12665518hexahydro-3-(3-oxocyclohexen-1-yl)-2H-azepin-2-oneYield 67.9%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Lithium diisopropylamide, prepared by treating diisopropylamine (45.3 ml) with 1.4 M butyl lithium in hexane (231 ml) at -10° C. under nitrogen, was treated at -60° C. with 1-trimethylsilylhexahydro-2H-azepin-2-one (63.7 g) in dry THF (50 ml). The white suspension was treated after 20 minutes with a solution of 3-methoxy-2-cyclohexenone (40.8 g) in THF (50 ml). The resulting solution was allowed to warm to ambient temperature. After a further 3 hours the cooled solution was treated with concentrated hydrochloric acid (120 ml) and stirred for 18 hours. The THF layer was combined with several chloroform extracts from the aqueous layer. Evaporation of the solvent gave a yellow solid, which was recrystallised from ethyl acetate to give hexahydro 3-(3-oxocyclohexen-1-yl) -2H-azepin-2-one as an off-white solid (45.5 g) m.p. 159°-165° C.

Workup

  1. customEvaporation of the solvent
  2. customgave a yellow solid, which
  3. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-84e007febc4043d99b29cd1be69a4b95
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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