Piperazine → 1-(2,4,5-Trimethylphenyl)piperazine

HRID 390003Notes

Reaction equation

HRID 390003 reaction equation
Br[C:2]1[C:3]([CH3:10])=[CH:4][C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.CC(C)([O-])C.[Na+]>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:10][C:3]1[CH:4]=[C:5]([CH3:9])[C:6]([CH3:8])=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 796101-Bromo-2,4,5-trimethylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 27608211-(2,4,5-Trimethylphenyl)piperazine

Reagents, catalysts & solvents 1

HCID 178424406HCID 178424406, compoundCatalyst

Procedure

A target compound (1.03 g, 5.041 mmol, 40.2%) was yielded in the same manner as Reference Example 10 by reacting 5-bromo-1,2,4-trimethylbenzene (2.5 g, 12.556 mmol) with piperazine (4.32 g, 50.224 mmol), sodium t-butoxide (1.75 g, 18.206 mmol) and dichlorobis(tri-o-tolylphosphine)palladium(II) (295.5 mg, 0.37 mmol) and purifying by separation through column chromatography (CH2Cl2/MeOH, 1:1).

Workup

  1. custompurifying by separation through column chromatography (CH2Cl2/MeOH, 1:1)

Sources & evidence

ORD record
ord-2e474e3faa344fab9691192b5a8b53f1
Source dataset
uspto-grants-2013_02
Patent number
US08383631B2

Reaction notes

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