1-(3-Aminopropyl)-4-methylpiperazine → HCID 21397163, compound

HRID 1414734Notes

Reaction equation

HRID 1414734 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.Cl[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1>C(O)C>[CH3:11][N:8]1[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 21397163HCID 21397163, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a two liter, three-necked flask fitted with condenser, dropping funnel, thermometer, magnetic stirrer and nitrogen inlet was placed 71.8 g. (0.456 mole) 1-(3-aminopropyl)-4-methyl piperazine and 150 ml. of ethanol. The solution was heated at reflux and a solution of 65.0 g. 2-chloro-3-nitropyridine dissolved in 500 ml. of warm ethanol was added dropwise over 90 minutes. The dark yellow reaction mixture was maintained at reflux of an additional hour then cooled to ambient temperature. The solvent was then removed in vacuo to obtain a yellow-brown semi-solid residue. The residue was partitioned between 200 ml. each of aqueous 1N HCl and methylene chloride, and aqueous phase washed with 100 ml. CH2Cl2. The aqueous portion was made basic with 6N NaOH and extracted with 3 × 250 ml. CH2Cl2. The combined organic layers were dried over Na2SO4 and the solvent evaporated to afford 2-[3-(4-methyl-1-piperazinyl)-propylamino]-3-nitropyridine as a red-yellow oil which crystallized on standing at room temperature; yield 82.9 g. (72%).

Workup

  1. customIn a two liter, three-necked flask fitted with condenser
  2. customthermometer, magnetic stirrer and nitrogen inlet was placed
  3. temperatureThe solution was heated
  4. temperatureat reflux
  5. temperatureThe dark yellow reaction mixture was maintained
  6. temperatureat reflux of an additional hour
  7. customThe solvent was then removed in vacuo
  8. customto obtain a yellow-brown semi-solid residue
  9. customThe residue was partitioned between 200 ml
  10. washeach of aqueous 1N HCl and methylene chloride, and aqueous phase washed with 100 ml
  11. extractionextracted with 3 × 250 ml
  12. dry with materialThe combined organic layers were dried over Na2SO4
  13. customthe solvent evaporated

Sources & evidence

ORD record
ord-3a6169f3d3164025ad50c1860275adf5
Source dataset
uspto-grants-1977_01
Patent number
US04002623

Reaction notes

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