Sodium Hydroxide → 3,4-Dihydrospiro[naphthalene-2(1H), 2'-piperidin]-1-one hydrochloride

HRID 1781506Notes

Reaction equation

HRID 1781506 reaction equation
C([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]#N)(=O)C1C=CC=CC=1.[Cl-:25].[Al+3].[Cl-].[Cl-].[OH-:29].[Na+]>ClCCCl>[ClH:25].[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]21[CH2:17][CH2:18][C:19]1[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:15]2=[O:29]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 190288501-Benzoyl-2-(2-phenylethyl)-2-piperidinecarbonitrile

Product 1

HCID 233610933,4-Dihydrospiro[naphthalene-2(1H), 2'-piperidin]-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 250 ml of 1,2-dichloroethane was dissolved 7.64 g of 1-benzoyl-2-(2-phenylethyl)-2-piperidinecarbonitrile. To this solution was added 8.0 g of aluminum chloride and the mixture was refluxed for 6 hours. The reaction mixture was then cooled and poured cautiously into 10% aqueous sodium hydroxide and extracted with methylene chloride and water. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was distilled off. To the group was added 100 ml of methanol and 100 ml of 20% aqueous sodium hydroxide and the mixture was refluxed for 12 hours. After cooling, methanol was distilled off and the group was extracted with methylene chloride and water. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was distilled off. The group was purified by alumina column chromatography using ethyl acetate-hexane (1:2) as the eluent. The active fraction was concentrated under reduced pressure and the group was treated with 6.0 ml of 4N-methanolic hydrochloric acid to give a solid. This solid was recrystallized from methylene chloride to provide 3.0 g of colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with methylene chloride and water
  4. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationthe solvent was distilled off
  7. additionTo the group was added 100 ml of methanol and 100 ml of 20% aqueous sodium hydroxide
  8. temperaturethe mixture was refluxed for 12 hours
  9. temperatureAfter cooling
  10. distillationmethanol was distilled off
  11. extractionthe group was extracted with methylene chloride and water
  12. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. distillationthe solvent was distilled off
  15. customThe group was purified by alumina column chromatography
  16. concentrationThe active fraction was concentrated under reduced pressure
  17. additionthe group was treated with 6.0 ml of 4N-methanolic hydrochloric acid
  18. customto give a solid
  19. customThis solid was recrystallized from methylene chloride

Sources & evidence

ORD record
ord-44fe0f9082374e0698078619b2803762
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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