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

HRID 1038720Notes

Reaction equation

HRID 1038720 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].[CH2:12]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([N:14]1[CH2:19][CH2:18][N:17]([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:16][CH2:15]1)[CH3:13]

Participants

5

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 11430Potassium CarbonateHCID 791961-Ethylpiperazine

Product 1

HCID 7925571-Ethyl-4-(4-nitrobenzyl)piperazineYield 99.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-nitrobenzylchloride (5 g, 29.14 mmol), N-ethylpiperazine (4.4 ml, 34.97 mmol, 1.2 eq.), potassium carbonate (8 g, 58.28, 2 eq.), and acetone (100 ml) is stirred for 15 h at reflux. The reaction mixture is allowed to cool to RT, filtered and concentrated to afford 7.2 g of the title compound as a brow oil: ESI-MS: 250.1 [MH]+; TLC: Rf=0.31 (DCM/MeOH+1% NH3aq, 9:1).

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-994243e6416545cba59d9a3eb0772b57
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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