HCID 70137390, compound → HCID 9794387, compound

HRID 1781363Notes

Reaction equation

HRID 1781363 reaction equation
C([N:3]1[CH2:8][CH2:7][C:6]2([CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:5][CH2:4]1)C>C(O)C.[OH-].[K+]>[O:18]=[C:9]1[C:6]2([CH2:7][CH2:8][NH:3][CH2:4][CH2:5]2)[CH2:17][CH2:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 1

HCID 70137390HCID 70137390, compound

Product 1

HCID 9794387HCID 9794387, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 1.84 g (6.4 mmoles) ethyl 3,4-dihydro-1-oxospiro[naphthalene-2(1H),4'piperidine] in 32 ml ethanol and 16 ml of 50% potassium hydroxide solution was heated at reflux for 18 hours. The solution was concentrated in vacuo to remove ethanol and the aqueous residue was extracted with 3×40 ml ether. The combined organic extracts were extracted with 2×40 ml 3N hydrochloric acid. The combined aqueous extracts were made basic with 10N sodium hydroxide and extracted with 3×75 ml ether. The combined organic extracts were washed with 20 ml water and brine, dried, and the solvent was removed in vacuo to give 1.07 g (78%) product as an oil;

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe solution was concentrated in vacuo
  3. customto remove ethanol
  4. extractionthe aqueous residue was extracted with 3×40 ml ether
  5. extractionThe combined organic extracts were extracted with 2×40 ml 3N hydrochloric acid
  6. extractionextracted with 3×75 ml ether
  7. washThe combined organic extracts were washed with 20 ml water and brine
  8. customdried
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1235741b27ab474a8d96b42ef5a69254
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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