Piperidine → 10-(1-Piperidinyl)-5H-dibenzo[a,d]cyclohepten-5-one

HRID 434698Notes

Reaction equation

HRID 434698 reaction equation
Br[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[O:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH:3]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[N:18]1([C:2]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:6](=[O:13])[C:5]3[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=3[CH:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1243721510-Bromo-5H-dibenzo[a,d][7]annulen-5-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 1109822610-(1-Piperidinyl)-5H-dibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 71.3 g of 10-bromo-5H-dibenzo[a,d]cyclohepten-5-one, 50 ml. of piperidine, 1 liter of t-butanol and finally 33.6 g of potassium t-butoxide was stirred under reflux 2 hours, then at room temperature overnight. The mixture was filtered, and concentrated to dryness. The residue was slurried with water and decanted. The residue was slurried with methanol and filtered to give 59.8 g of 10-(1-piperidyl)-5H-dibenzo[a,d]cyclohepten-5-one, m.p. 103°-105° C.

Workup

  1. temperatureunder reflux 2 hours
  2. customat room temperature
  3. customovernight
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated to dryness
  6. customdecanted
  7. filtrationfiltered

Sources & evidence

ORD record
ord-0f26040b80254976847da16edf57f8f8
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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