Hydrochloric Acid → 4-(Piperidin-1-yl)aniline dihydrochloride

HRID 1079393Notes

Reaction equation

HRID 1079393 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[ClH:16]>CO.[Pd]>[ClH:16].[ClH:16].[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 81049Piperidine, 1-(4-nitrophenyl)-

Product 1

HCID 233669404-(Piperidin-1-yl)aniline dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(4-nitrophenyl)piperidine (12 g) in methanol (50 ml) was added conc. hydrochloric acid (12 ml) and, by using 10% palladium/carbon as a catalyst, catalytic reduction was conducted at normal temperature and normal pressure. After completion of the reaction, the catalyst was removed and the solvent was distilled off. To the residue was added ethyl ether which was filtered off to obtain N-(4-aminophenyl)piperidine dihydrochloride (13.7 g) as a colorless solid.

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed
  3. distillationthe solvent was distilled off
  4. additionTo the residue was added ethyl ether which
  5. filtrationwas filtered off

Sources & evidence

ORD record
ord-a5f5f430f6224521ad1d3827cde920c7
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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