1-Ethyl-4-(4-nitrophenyl)piperidine → 4-(1-Ethyl-piperidin-4-yl)phenylamine

HRID 409676Notes

Reaction equation

HRID 409676 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]>[Pd].CCO>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 691793941-Ethyl-4-(4-nitrophenyl)piperidine

Product 1

HCID 671709894-(1-Ethyl-piperidin-4-yl)phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-ethyl-4-(4-nitro-phenyl)-piperidine (0.8 g, 4.92 mmol) and 10% palladium on carbon (0.1 g) in EtOH (10 mL) is stirred for 3 h at RT, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5) to provide the title compound. ESI-MS: 205.1 [MH]+; TLC: Rf=0.29 (DCM/MeOH+1% NH3aq, 95:5).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated
  3. customThe residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5)

Sources & evidence

ORD record
ord-42b019557856409d9a18b71c651e613b
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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