1-Methyl-4-(1-(4-nitrophenyl)piperidin-4-yl)piperazine → 4-(4-(4-Methyl-1-piperazinyl)-1-piperidinyl)benzenamine

HRID 2189267Notes

Reaction equation

HRID 2189267 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 580159221-Methyl-4-(1-(4-nitrophenyl)piperidin-4-yl)piperazine

Product 1

HCID 580157484-(4-(4-Methyl-1-piperazinyl)-1-piperidinyl)benzenamineYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-4-yl]-piperazine-(46 mg, 0.15 mmol) and Pd/C (10%, 8 mg) in MeOH (2 mL) is stirred at room temperature under H2 (balloon pressure) for 16 hours, then filtered through celite, washed with EtOAc, concentrated under reduced pressure to give 42 mg of the title compound as a light grey solid.

Workup

  1. filtrationfiltered through celite
  2. washwashed with EtOAc
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfbce55ba50f463fbfe303b9c609dbb8
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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