2-Chloro-5-nitropyridine → 1-Ethyl-4-(5-nitropyridin-2-yl)piperazine

HRID 2042210Notes

Reaction equation

HRID 2042210 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH3:12].C(N(CC)C(C)C)(C)C>O1CCOCC1.C(OCC)(=O)C>[CH2:11]([N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:15][CH2:14]1)[CH3:12]

Participants

6

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 791961-EthylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 28489801-Ethyl-4-(5-nitropyridin-2-yl)piperazineYield 88%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloro-5-nitropyridine (800 mg, 5.05 mmol) was dissolved in dioxane (20 mL) and then 1-ethylpiperazine (1.7 g, 15.15 mmol) and N,N-diisopropylethylamine (927 mL, 5.05 mmol) were added. The reaction mixture solution was stirred at 70° C. for a day. The reaction solution was cooled to room temperature, diluted with ethyl acetate, and then washed with brine. The organic layer was concentrated by drying with magnesium sulfate. The target compound (1.05 g, 87% yield) was used in the following reaction without purification.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washwashed with brine
  3. concentrationThe organic layer was concentrated
  4. dry with materialby drying with magnesium sulfate

Sources & evidence

ORD record
ord-27c945d55a6245ecad8134a2572a5ecb
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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