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

HRID 975114Notes

Reaction equation

HRID 975114 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.C(Cl)Cl.O>[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

7

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 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In 250 ml of 1,2-dichloroethane was dissolved 7.64 g of 1-benzoyl-2-(2-phenylethyl)-2piperidinecarbonitrile. Then, 8.0 g of aluminum chloride was added and the mixture was refluxed for 6 hours. The reaction mixture was cooled and poured cautiously into 10% aqueous sodium hydroxide solution. Then, methylene chloride and water were added for extraction. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was distilled off. To the residue were added 100 ml of methanol and 100 ml of 20% aqueous sodium hydroxide solution and the mixture was refluxed for 12 hours. After the reaction mixture was allowed to cool, the methanol was distilled off and methylene chloride and water were added for extraction. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was then distilled off. The residue was purified by alumina column chromatography using an ethyl acetate-hexane solvent system and the eluate containing the desired compound was distilled under reduced pressure. The residue was treated with 6.0 ml of 4N-methanolic HCl to provide a solid. This solid was recrytallized 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 cooled
  3. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off
  6. additionTo the residue were added 100 ml of methanol and 100 ml of 20% aqueous sodium hydroxide solution
  7. temperaturethe mixture was refluxed for 12 hours
  8. temperatureto cool
  9. distillationthe methanol was distilled off
  10. additionmethylene chloride and water were added for extraction
  11. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. distillationthe solvent was then distilled off
  14. customThe residue was purified by alumina column chromatography
  15. additionthe eluate containing the desired compound
  16. distillationwas distilled under reduced pressure
  17. additionThe residue was treated with 6.0 ml of 4N-methanolic HCl
  18. customto provide a solid

Sources & evidence

ORD record
ord-358523a15cf142819764e47e45760ea1
Source dataset
uspto-grants-1997_03
Patent number
US05607939

Reaction notes

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