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

HRID 1515129Notes

Reaction equation

HRID 1515129 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[OH-].[Na+].[Na+].[Cl-].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>O>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=2)[NH2:7])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 27600345-(4-Methylpiperazin-1-yl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

To a 4-dram vial was added 5-Chloro-2-nitroaniline (0.5 g, 2.90 mmol, 1 equiv.), NaOH (0.229 g, 5.71 mmol, 1.98 equiv.), 4′M NaCl (0.82 mL, aq.), and 1-methylpiperazine (0.643 g, 0.71 mL, 5.79 mmol, 2 equiv.). The mixture was heated on a hot plate to 105° C. for 22 h. De-ionized H2O (6 mL) was added to the mixture, which was cooled to room temperature, and the precipitate collected on a Buchner funnel. The precipitate was then washed with de-ionized H2O (5 mL) and heptane (5 mL). After drying in a vacuum oven (80° C., 30 in. Hg) overnight, the product (0.624 g, 91.1%) was collected. According to HPLC analysis, the sample had a purity of 99.6%.

Workup

  1. temperaturewas cooled to room temperature
  2. customthe precipitate collected on a Buchner funnel
  3. washThe precipitate was then washed with de-ionized H2O (5 mL) and heptane (5 mL)
  4. customAfter drying in a vacuum oven (80° C., 30 in. Hg) overnight
  5. customthe product (0.624 g, 91.1%) was collected

Sources & evidence

ORD record
ord-2c35e400f46641f29c071a4cb5f5acea
Source dataset
uspto-grants-2012_07
Patent number
US08222413B2

Reaction notes

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