1-(4-Nitrophenyl)piperidin-4-one → 1-(4-Aminophenyl)piperidin-4-one

HRID 450057Notes

Reaction equation

HRID 450057 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][C:13](=[O:16])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 38425621-(4-Nitrophenyl)piperidin-4-one

Product 1

HCID 222202411-(4-Aminophenyl)piperidin-4-oneYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(4-nitro-phenyl)-piperidin-4-one (150 mg, 0.68 mmol) was dissolved in methanol (4 ml) and hydrogenated over 10% Pd/C (20 mg) at atmospheric pressure until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to yield the crude compound, which was purified by column chromatography using ethyl acetate/hexane (3:2) to give 1-(4-aminophenyl)-piperidin-4-one (75 mg, 57%).

Workup

  1. filtrationThe reaction mixture was then filtered over celite and
  2. concentrationconcentrated
  3. customto yield the crude compound, which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-843e582992414cdf8023e3a7b28331ab
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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