Ethanol → 1-(4-Aminophenyl)piperidin-4-ol

HRID 57640Notes

Reaction equation

HRID 57640 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-].CCO>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([OH:16])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 6137681-(4-Nitrophenyl)-4-piperidinol

Product 1

HCID 167921071-(4-Aminophenyl)piperidin-4-olYield 44%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1-(4-nitrophenyl)piperidin-4-ol (4.725 g, 21.26 mmol), Fe (11.87 g, 212.6 mmol), NH4Cl (11.41 g, 212.6 mmol), EtOH (100 mL) and water (50 mL) were mixed. The mixture was stirred at 100° C. overnight. Then Fe (5.9 g, 106.3 mmol) was added and reacted at 100° C. for 7 hours. Filtrated and the liquid was concentrated, purified by flash chromatography to give 1.8 g yellow solid.

Workup

  1. customreacted at 100° C. for 7 hours
  2. filtrationFiltrated
  3. concentrationthe liquid was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1865476250934b90ad72ceadeaf52e9d
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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