Pyridine → Benzyl 4-(3-nitropyridin-2-yl)piperazine-1-carboxylate

HRID 1449720Notes

Reaction equation

HRID 1449720 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].N1C=CC=CC=1.[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:22]([O:29][C:30]([N:13]1[CH2:12][CH2:11][N:10]([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:15][CH2:14]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 37788341-(3-Nitropyridin-2-yl)piperazine

Product 1

HCID 21477687Benzyl 4-(3-nitropyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Nitro-2-pyridinyl)piperazine is dissolved in 175 ml of methylene chloride and cooled to 0°. Then pyridine is added followed by benzylchloroformate (16.5 ml). The reaction is stirred 1.5 hr, then poured into saturated aqueous sodium bicarbonate and extracted with chloroform, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound, NMR (300 MHz, CDCl3) 8.34, 8.15, 7.38-7.32, 6.81, 5.17, 3.65 and 3.45 δ.

Workup

  1. temperaturecooled to 0°
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-729fe896f2944f85a2eeab1714eb1166
Source dataset
uspto-grants-1997_02
Patent number
US05599930

Reaction notes

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