Tert-butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate → Tert-butyl 4-(3-methyl-4-aminophenoxy)piperidine-1-carboxylate

HRID 1268177Notes

Reaction equation

HRID 1268177 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)=[C:17]([CH3:24])[CH:16]=2)[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])=[C:17]([CH3:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 18542679Tert-butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 18542772Tert-butyl 4-(3-methyl-4-aminophenoxy)piperidine-1-carboxylateYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-2-methylnitrobenzene (3.23 g) in methanol (30 ml) was added palladium on carbon (0.21 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=1/1 as an eluant to give the desired compound (3.02 g, yield 99%) 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-ca2910c5c82f464197ced4fdae01ad99
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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