HCID 18542692, compound → HCID 18542763, compound

HRID 1268226Notes

Reaction equation

HRID 1268226 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([N+:22]([O-])=O)=[CH:17][C:16]=2[CH3:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.O1CCCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:16]([CH3:25])=[CH:17][C:18]([NH2:22])=[CH:19][C:20]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 18542692HCID 18542692, compound

Product 1

HCID 18542763HCID 18542763, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3,5-dimethylnitrobenzene (2.24 g) in a mixture of ethanol (30 ml) and tetrahydrofuran (10 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 (1.94 g, yield 95%) as a pale rose 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-9abac3f66b4040288146796c2e1af8be
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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