4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3,5-difluoronitrobenzene → 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3,5-difluoroaniline

HRID 1268223Notes

Reaction equation

HRID 1268223 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([N+:22]([O-])=O)=[CH:17][C:16]=2[F:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[C:16]([F:25])=[CH:17][C:18]([NH2:22])=[CH:19][C:20]=2[F:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 185427114-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3,5-difluoronitrobenzene

Product 1

HCID 185427744-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3,5-difluoroanilineYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3,5-difluoronitrobenzene (2.13 g) in ethanol (40 ml) was added palladium on carbon (0.20 g) and the mixture was stirred under a hydrogen atmosphere at room temperature for 1 hour. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=2/1 as an eluant to give the desired compound (1.70 g, yield 87%) as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-98be2e64b7a8440abd26dc0e5c76d408
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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