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

HRID 2049335Notes

Reaction equation

HRID 2049335 reaction equation
C([Li])CCC.[C:6]1(=[O:13])[NH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C[O:15][C:16]1[CH2:21][CH2:20][CH2:19][C:18](=O)[CH:17]=1.Cl>O1CCCC1>[O:15]=[C:16]1[CH2:21][CH2:20][CH2:19][C:18]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:6]2=[O:13])=[CH:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7768CaprolactamHCID 855973-Methoxycyclohex-2-en-1-oneHCID 178418339Butyllithium

Product 1

HCID 12665518hexahydro-3-(3-oxocyclohexen-1-yl)-2H-azepin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyllithium (143 ml of 1.4 molar solution in hexane) was added dropwise to a stirred solution of caprolactam (11.3 g) in dry tetrahydrofuran under nitrogen. After stirring for 50 minutes at 0°, 3-methoxy-2-cyclohexenone (12.6 g) in tetrahydrofuran was added. After a further 30 minutes the reaction was poured onto 5 M hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with chloroform. The combined organic layers were dried over magnesium sulphate. Removal of the solvent under reduced pressure left 15 g of a yellow solid. The product was recrystallised from ethyl acetate affording 2.5 g of the title compound identical to that described in Example 17.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. customRemoval of the solvent under reduced pressure
  5. waitleft 15 g of a yellow solid
  6. customThe product was recrystallised from ethyl acetate affording 2.5 g of the title compound identical to

Sources & evidence

ORD record
ord-f74775f592414618bc3501845a659f52
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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