Potassium Carbonate → 1-Methyl-4-(3-nitrobenzyl)piperazine

HRID 2066691Notes

Reaction equation

HRID 2066691 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12078alpha-Chloro-m-nitrotolueneHCID 531671-Methylpiperazine

Product 1

HCID 13771091-Methyl-4-(3-nitrobenzyl)piperazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-nitrobenzylchloride (5 g, 29.14 mmol), N-methylpiperazine (3.9 mL, 34.97 mmol, 1.2 equiv), potassium carbonate (8 g, 58.28, 2 equiv), and acetone (100 ml) is stirred for 15 h at reflux. The reaction mixture is allowed to cool to RT, filtered and concentrated. The residue is purified by silica gel MPLC (DCM/MeOH+1% NH3aq, 95:5) to afford the title compound as a brow oil: ESI-MS: 236.0 [MH]+; tR=1.40 min (purity: 100%, system 1); TLC: Rf=0.31 (DCM/MeOH+1% NH3aq, 9:1).

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel MPLC (DCM/MeOH+1% NH3aq, 95:5)

Sources & evidence

ORD record
ord-ef8f71e0e28041f2bb787a6df9c4282d
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

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