tert-Butyl 4-(2-methyl-4-nitrophenoxy)piperidine-1-carboxylate → Tert-butyl 4-(4-amino-2-methylphenoxy)piperidine-1-carboxylate

HRID 1268186Notes

Reaction equation

HRID 1268186 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][C:16]=2[CH3:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>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][C:16]=2[CH3:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22181075tert-Butyl 4-(2-methyl-4-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 22181171Tert-butyl 4-(4-amino-2-methylphenoxy)piperidine-1-carboxylateYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-methylnitrobenzene (4.07 g) in methanol (40 ml) was added palladium on carbon (0.41 g) and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hours. 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=3/2 as an eluant to give the desired compound (2.73 g, two step yield, from Reference example 41, 53%) as a pale red oil.

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-102972cfdde049aa903d8d589b97e7da
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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