Acetic Acid → 4-Phenyl-1-(4-carboxyphenyl)piperidine

HRID 478350Notes

Reaction equation

HRID 478350 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17]C(C#N)=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:22]([OH:25])(=[O:24])[CH3:23]>>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:18]=[CH:17][C:23]([C:22]([OH:25])=[O:24])=[CH:15][CH:14]=3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 180010564-Phenyl-1-(4-cyanophenyl)piperidine

Product 1

HCID 180010494-Phenyl-1-(4-carboxyphenyl)piperidine

Procedure

To 4-phenyl-1-(4-cyanophenyl)piperidine (0.39 g) are added acetic acid (10 ml) and conc. hydrochloric acid (10 ml), and the mixture is refluxed for five hours. The reaction solution is concentrated, and to the residue is added diethyl ether/methanol. The insoluble crystals are collected by filtration, and dried under reduced pressure to give 4-phenyl-1-(4-carboxyphenyl)piperidine (0.39 g) as white powder.

Workup

  1. temperaturethe mixture is refluxed for five hours
  2. concentrationThe reaction solution is concentrated
  3. additionto the residue is added diethyl ether/methanol
  4. filtrationThe insoluble crystals are collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-32620f07c2644768afd7313bfeea8448
Source dataset
uspto-grants-2003_11
Patent number
US06642223B2

Reaction notes

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