4-Nitrobenzyl chloride → 1-Isopropyl-4-(4-nitrobenzyl)piperazine

HRID 43057

Reaction equation

HRID 43057 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:12]([N:15]1[CH2:20][CH2:19][N:18]([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:17][CH2:16]1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 11430Potassium CarbonateHCID 780131-Isopropylpiperazine

Product 1

HCID 8826511-Isopropyl-4-(4-nitrobenzyl)piperazineYield 90.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-nitrobenzylchloride (4.1 g, 23.90 mmol), N-isopropylpiperazine (3.6 g, 28.67 mmol, 1.2 equiv), potassium carbonate (6.5 g, 47.79 mmol, 2 equiv) and acetone (82 ml) was stirred for 16 h at reflux. The reaction mixture was allowed to cool, was then filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) to afford 5.7 g of the title compound: ESI-MS: 264.1 [M+H]+; TLC: tR=1.73 min (System 1); TLC: Rf=0.34 (DCM/MeOH+1% NH3aq, 9:1).

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. filtrationwas then filtered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)

Sources & evidence

ORD record
ord-078e0ec21f6f4cd6a82c0fa59bcb545b
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Linked notes

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