Piperazine → HCID 602112, compound

HRID 349664Notes

Reaction equation

HRID 349664 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][C:6]=1[NH2:8])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 602112HCID 602112, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (4.3 g, 25 mmol), piperazine (12.5 g, 145 mmol), and K2CO3 (4.0 g, 29 mmol) in DMF (50 mL) was stirred at 150° C. for 18 h. The reaction mixture was cooled to room temperature, solids were removed by filtration, and the filtrate was concentrated to a red residue. The residue was dissolved in EtOAc (100 mL), washed with water (50 mL), dried with Na2SO4, and concentrated in vacuo to afford the product as a yellow solid (3.9 g, 70%). See, Pharmazie, 39:747 (1984).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customsolids were removed by filtration
  3. concentrationthe filtrate was concentrated to a red residue
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. washwashed with water (50 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-285ac8c3a8594d609fbb81d13f73c4ef
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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