1-Methylpiperazine → HCID 71239102, compound

HRID 1842683Notes

Reaction equation

HRID 1842683 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6]N[CH2:4][CH2:3]1.[CH3:8][O:9][C:10]1[CH:18]=[C:17]([N+:19]([O-])=O)[C:16]([N+:22]([O-:24])=[O:23])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>O>[CH3:8][O:9][C:10]1[CH:18]=[C:17]([N:19]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[C:16]([N+:22]([O-:24])=[O:23])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 531671-Methylpiperazine2×HCID 21133888HCID 21133888, compound

Product 1

HCID 71239102HCID 71239102, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1-Methylpiperazine (0.962 mL, 8.67 mmol) was added to a suspension of 2-methoxy-4,5-dinitrobenzoic acid (2.0 g, 8.26 mmol) in water (5 mL). The mixture was heated at 50° C. for 1.5 h then 75° C. for 3 h. A further 0.5 equivalents of 1-methylpiperazine was added and the mixture was heated overnight. The mixture was then allowed to cool and stand. A crystalline solid formed which was collected by filtration, washed with water and then dried on the filter to give the title compound (1.87 g, 77%) as a yellow crystalline solid; 1H NMR: 2.25 (3H, s), 2.45-2.49 (4H, m), 3.13-3.21 (4H, m), 3.93 (3H, s), 6.63 (1H, s), 8.32 (1H, s); m/z: ES+ MH+ 296.5.

Workup

  1. temperaturethe mixture was heated overnight
  2. temperatureto cool
  3. customA crystalline solid formed which
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried on the
  7. filtrationfilter

Sources & evidence

ORD record
ord-7af4762e10e94c34840dd691ceef9aac
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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