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

HRID 1079402Notes

Reaction equation

HRID 1079402 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]>C(O)C.[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 106.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-tert-butyloxycarbonyl-4-(4-nitro-2-methylphenyloxy)piperidine (9.0 g) in ethanol (100 ml) was added conc. hydrochrolic acid (2.3 ml) and, by using 10% palladium/carbon (containing 48% of water, 1 g) as a catalyst, catalytic reduction was conducted under normal pressure for 1.5 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to obtain 1-tert-butyloxycarbonyl-4-(4-amino-2-methylphenyloxy)piperidine (8.7 g) as a light brown amorphous material.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e903dcc1d2bd44aba547b79b35ab622e
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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