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

HRID 412540Notes

Reaction equation

HRID 412540 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]>O1CCCC1.C(O)C.[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 1

HCID 2794776Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylateYield 86.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Nitrophenoxy)piperidine-1-carboxylic acid tert-butyl ester (53.687 g) was hydrogenated using 7.5% palladium carbon (8.05 g) in a mixture of tetrahydrofuran (215 ml) and ethanol (215 ml) at 3 atm over 3 hours. After completion of the reaction, the reaction mixture was filtered through celite and the solvent was evaporated. Hexane was added to the obtained residue, and the obtained solid was collected by filtration and dried under reduced pressure to give the title compound (42.157 g).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. customthe solvent was evaporated
  4. additionHexane was added to the obtained residue
  5. filtrationthe obtained solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5d8a9c5f3d0148e5a7d9e430138ebd94
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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