Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate → tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

HRID 747774Notes

Reaction equation

HRID 747774 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2794776Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2.74 g (8.5 mmol) of 1-t-butoxycarbonyl-4-(4-nitrophenoxy)piperidine was dissolved in 20 ml of ethanol. 20 mg of 10% palladium/carbon was added to the solution, and they were stirred at room temperature in 1 atm. hydrogen atmosphere for 3 hours. Palladium/carbon was removed by the suction filtration. The filtrate was once concentrated and then treated with dichloromethane as extractant in an ordinary manner to obtain the title compound.

Workup

  1. customPalladium/carbon was removed by the suction filtration
  2. concentrationThe filtrate was once concentrated
  3. additiontreated with dichloromethane as extractant in an ordinary manner

Sources & evidence

ORD record
ord-aca25c323e6c47a5a53c06ec71df4fe2
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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