Spiro(1-indanon)-2,4'-(piperidine), N-benzoyl- → Spiro[indene-2,4'-piperidin]-1(3H)-one

HRID 1591153Notes

Reaction equation

HRID 1591153 reaction equation
C([N:9]1[CH2:14][CH2:13][C:12]2([CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:23])[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1>C(O)C.Cl>[O:23]=[C:15]1[C:12]2([CH2:13][CH2:14][NH:9][CH2:10][CH2:11]2)[CH2:22][C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2

Participants

4

Reactant 1

HCID 680371Spiro(1-indanon)-2,4'-(piperidine), N-benzoyl-

Product 1

HCID 19085830Spiro[indene-2,4'-piperidin]-1(3H)-oneYield 77.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent

Procedure

A solution of 3.66 g (12.0 mmoles) 1'-benzoyl-1,3-dihydro-1-oxospiro-[2H-indene-2,4'-piperidine] in 90 ml ethanol and 30 ml 6N hydrochloric acid was heated at reflux for 42 hours. An additional 10 ml 6N hydrochloric acid was added and the solution was heated at reflux for 6 hours. The cooled solution was concentrated in vacuo to remove ethanol and the resulting aqueous solution was washed with 2×20 ml ethyl acetate. The aqueous layer was made basic with 10N sodium hydroxide and extracted with 3×75 ml ethyl acetate. The extract was washed with 20 ml water and brine, dried, and the solvent was removed in vacuo to give 1.87 g (77%) product as an oil.

Workup

  1. temperatureat reflux for 42 hours
  2. temperaturethe solution was heated
  3. temperatureat reflux for 6 hours
  4. concentrationThe cooled solution was concentrated in vacuo
  5. customto remove ethanol
  6. washthe resulting aqueous solution was washed with 2×20 ml ethyl acetate
  7. extractionextracted with 3×75 ml ethyl acetate
  8. washThe extract was washed with 20 ml water and brine
  9. customdried
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0533bac767bf4c618aba9a7c17542ca7
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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