Potassium Carbonate → hexahydro-1-[2-(4-methoxyphenyl)ethyl]-4H-azepin-4-one

HRID 968488Notes

Reaction equation

HRID 968488 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:21][CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+]>Cl.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:21][CH2:20][CH2:19][C:14](=[O:15])[CH2:13][CH2:12]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 692829498-[2-(4-Methoxyphenyl)ethyl]-1,4-dioxa-8-azaspiro[4.6]undecane

Product 1

HCID 69282946hexahydro-1-[2-(4-methoxyphenyl)ethyl]-4H-azepin-4-oneYield 93.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of intermediate (6) (0.098 mol) in HCl (3 N, 300 ml) and THF (300 ml) was stirred at 60° C. for 1 hour. The mixture was basified with solid K2CO3 and extracted with ethyl acetate. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 22.6 g of hexahydro-1-[2-(4-methoxyphenyl)ethyl]-4H-azepin-4-one (intermediate 7).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2ae045344984407ca46a2b8df1f9ddfa
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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