1-Benzoyl-4-benzylpiperidine-4-carboxylic acid → Spiro(1-indanon)-2,4'-(piperidine), N-benzoyl-

HRID 1781357Notes

Reaction equation

HRID 1781357 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][C:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:15](O)=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[C:1]([N:9]1[CH2:14][CH2:13][C:12]2([CH2:18][C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:15]2=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 222406641-Benzoyl-4-benzylpiperidine-4-carboxylic acid

Product 1

HCID 680371Spiro(1-indanon)-2,4'-(piperidine), N-benzoyl-Yield 62.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.14 g (19.0 mmoles) 1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylic acid in 61 ml concentrated sulfuzic acid was stirred 18 hours at room temperature to give a deep red solution. The solution was carefully diluted with ice-bath cooling with 300 ml H2O and extracted with 3×300 ml ethyl acetate. The extract was washed with 25 ml water and brine, dried, and the solvent wam removed in vacuo to give a white foam. The foam was stirred under ether and filtered off to give 3.61 g (62%) product, m.p. 149°-154° C. 1H NMR (deuteriochloroform): δ1.50 (m, 2H), 2.00 (m, 2H), 3.12 (m, 2H), 3.25 (d of d of d, 2H), 3.90 (d, 1H), 4.62 (m, 1H), 7.43 (m, 7H), 7.63 (d of d, 1H), 7.79 (d, 1H).

Workup

  1. customto give a deep red solution
  2. additionThe solution was carefully diluted with ice-bath
  3. extractionextracted with 3×300 ml ethyl acetate
  4. washThe extract was washed with 25 ml water and brine
  5. customdried
  6. customthe solvent wam removed in vacuo
  7. customto give a white foam
  8. stirringThe foam was stirred under ether
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-912fda52d8fa431a8028fa3907b7ca92
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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