1-Isopropyl-4-(4-nitrophenyl)piperazine → 4-[4-(Propan-2-yl)piperazin-1-yl]aniline

HRID 409670Notes

Reaction equation

HRID 409670 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]>[Pd].CO>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 98347891-Isopropyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 91615454-[4-(Propan-2-yl)piperazin-1-yl]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-isopropyl-4-(4-nitro-phenyl)-piperazine (5.18 g, 20.80 mmol) and 5% palladium on carbon (0.5 g) in MeOH (100 mL) is stirred for 2.7 h at RT, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated to afford the title compound as a violet solid: ESI-MS: 220.1 [MH]+; tR=0.95 min (system 1).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5ddd32a0c94c4555a84130c272e9d7bd
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

Loading…