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

HRID 1700296Notes

Reaction equation

HRID 1700296 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.CO.[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

6

Reactant 2

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

Product 1

HCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylateYield 85.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A slurry of 4-(N-(t-butoxycarbonyl)piperidin-4-yl)oxy-1-nitrobenzene (15.1 g, 46.8 mmol) in absolute ethanol (500 mL) and methanol (200 mL) was purged with nitrogen, treated with 10% palladium on carbon (1.2 g, 50% water by wt.) and placed on a Parr Hydrogenator under 43 psi of hydrogen gas. The catalyst was removed by filtration. Solvent removal under reduced pressure gave a solid after drying. Purification by flash silica gel chromatography using a step gradient of 50 to 85% ethyl acetate in hexane gave 11.7 g of 4-(N-(t-butoxycarbonyl)piperidin-4-yl)oxybenzenamine, NMR (CDCl3, TMS) δ1.45 (s, 9), 1.7 (m, 2), 1.86 (m, 2), 3.25 (m, 2), 3.68 (m, 2), 4.25 (m, 1), 6.63 (m, 2), 6.76 (m, 2).

Workup

  1. customThe catalyst was removed by filtration
  2. customSolvent removal under reduced pressure
  3. customgave a solid
  4. customafter drying
  5. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-9120f7165cca456ca394b3e9d85fe046
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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