1-(4-Nitrophenyl)-4-piperidinol → 1-(4-Aminophenyl)piperidin-4-ol

HRID 538008Notes

Reaction equation

HRID 538008 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[H][H]>CO.O1CCCC1.[C].[Pd]>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 6137681-(4-Nitrophenyl)-4-piperidinolHCID 178418361HCID 178418361, compound

Product 1

HCID 167921071-(4-Aminophenyl)piperidin-4-ol

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 4-hydroxy-N-(4-nitrophenyl)piperidine (11.1 g, 50 mmol) obtained in Example 1(1) was dissolved in methanol (100 ml) and tetrahydrofuran (50 ml), and 10% palladium-carbon (8.0 g) was added thereto, followed by stirring at room temperature in an atmosphere of hydrogen gas for 7 hours. After the insoluble material was filtered with Celite, the filtrate was concentrated under reduced pressure, diethyl ether was added to the obtained residue, and the precipitate was collected by filtration, thereby obtaining 4-hydroxy-N-(4-aminophenyl)piperidine (9.25 g, 94%) as a reddish-purple solid.

Workup

  1. filtrationAfter the insoluble material was filtered with Celite
  2. concentrationthe filtrate was concentrated under reduced pressure, diethyl ether
  3. additionwas added to the obtained residue
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-fbcaf3d7bfc54d948e4b438198483c19
Source dataset
uspto-grants-2014_10
Patent number
US08865714B2

Reaction notes

Loading…