1-Methylpiperazine → 1-Methyl-4-(5-nitropyridin-2-yl)piperazine

HRID 268252

Reaction equation

HRID 268252 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C(O)C>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 27640661-Methyl-4-(5-nitropyridin-2-yl)piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A 500 ml. 3-neck, r.b. flask fitted with y-tube and condenser and thermometer, stirrer and addition funnel was charged with a mixture of 2-chloro-5-nitropyridine (15.8 g. 0.1 mole) in ethanol (300 ml.). To this was added N-methylpiperazine (20 g. 0.2 mole) dropwise while stirring. After the addition (ca. 5 min.), the mixture was heated at reflux for 3 hr. while stirring continued. The solution was chilled to 5°C and the crystals were collected by filtration and dried at 60°C to yield 12 g. yellow crystals, m.p. 94°-96°C.

Workup

  1. customflask fitted with y-tube and condenser and thermometer, stirrer and addition funnel
  2. additionAfter the addition (ca. 5 min.)
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 3 hr
  5. stirringwhile stirring
  6. filtrationthe crystals were collected by filtration
  7. customdried at 60°C
  8. customto yield 12 g

Sources & evidence

ORD record
ord-7fc1113a06b84f7ba20783a28fe98238
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Linked notes

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