Piperazine → 1-(2-Chloro-4-nitrophenyl)piperazine

HRID 2291557Notes

Reaction equation

HRID 2291557 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.O1CCOCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 74431,2-Dichloro-4-nitrobenzeneHCID 312751,4-Dioxane

Product 1

HCID 27713311-(2-Chloro-4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4-Dichloronitrobenzene (10 g), piperazine (30 g) and dioxan (10 ml) were stirred for 4 hours under gentle reflux (internal temp. 120°-130°). The mixture was then cooled and water (50 ml) was added; the desired product crystallized out and was filtered off, washed with water and dried: yield of the compound 11.32 g. A small portion (0.6 g) was recrystallized from petroleum b.p. 60°-80°/ethyl acetate, yielding the product, (0.36 g), m.p. 100°-102°.

Workup

  1. temperatureunder gentle reflux (internal temp. 120°-130°)
  2. temperatureThe mixture was then cooled
  3. customthe desired product crystallized out and
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried
  7. customA small portion (0.6 g) was recrystallized from petroleum b.p. 60°-80°/ethyl acetate
  8. customyielding the product, (0.36 g), m.p. 100°-102°

Sources & evidence

ORD record
ord-7878259e078e48e58ccf5db9739d902a
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

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