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

HRID 1661013Notes

Reaction equation

HRID 1661013 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 98.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-nitrobenylchloride (4.1 g, 23.90 mmol), N-isopropylpiperazine (3.6 g, 28.67 mmol, 1.2 eq.), potassium carbonate (6.5 g, 47.79, 2 equiv), and acetone (82 mL) is stirred for 16 h at reflux. The reaction mixture is allowed to cool to rt, filtered and concentrated. Purification of the residue by silica gel column chromatography (CH2Cl2/MeOH+1% NH3aq, 9:1) affords 6.2 g of the title compound as a yellow solid: to afford the title compound as a yellow solid: ESI-MS: 264.1 [M+H]+; tR=1.73 min (System 1); TLC: Rf=0.34 (CH2Cl2/MeOH+1% NH3aq, 9:1).

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification of the residue by silica gel column chromatography (CH2Cl2/MeOH+1% NH3aq, 9:1)

Sources & evidence

ORD record
ord-e176ed747ecc45ad988fdc92807c72d8
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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