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

HRID 1249977Notes

Reaction equation

HRID 1249977 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-a5a20b236748481cb3c748029857654f
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

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