Sodium Hydroxide → 5-(4-Methylpiperazin-1-yl)-2-nitroaniline

HRID 1515128Notes

Reaction equation

HRID 1515128 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Cl[C:11]1[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([CH:17]=1)[NH2:16]>>[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([CH:17]=2)[NH2:16])[CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 531671-MethylpiperazineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 27600345-(4-Methylpiperazin-1-yl)-2-nitroanilineYield 99%

Procedure

The mother liquor of the reaction was recycled by the addition of NaOH pellets (34.9 g, 869 mmol, 1 equiv) to the mother liquor, followed by stirring until the NaOH was dissolved. 1-Methylpiperazine (96.5 mL, 869 mmol, 1 equiv) and 5-chloro-2-nitroaniline (150 g, 869 mmol) were charged to the vessel. Purging, followed by heating to completion, cooling, filtration, and washing with heptane was repeated as above to yield 5-(4-methyl-piperazin-1-yl)-2-nitroaniline (203.2 g, 98.9% yield). Residual N-methylpiperazine was not detected by 1H NMR.

Workup

  1. dissolutionwas dissolved
  2. customPurging
  3. temperatureby heating to completion
  4. temperaturecooling
  5. filtrationfiltration
  6. washwashing with heptane

Sources & evidence

ORD record
ord-95d9d03021054ab1bfc8c933f1ad21d2
Source dataset
uspto-grants-2012_07
Patent number
US08222413B2

Reaction notes

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