Piperidine → 5-Bromo-3-nitro-2-(piperidin-1-yl)pyridine

HRID 1431340Notes

Reaction equation

HRID 1431340 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 467387925-Bromo-3-nitro-2-(piperidin-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a 100 mL round bottom flask containing 5-bromo-2-chloro-3-nitropyridine (5.05 g, 21.3 mmol) in DMSO (20 mL) was added piperidine (4.2 mL, 42.6 mmol) dropwise. The reaction was heated to 60° C. and monitored with TLC and LC-MS. After 2.5 h, LC-MS showed that the reaction was complete. The mixture was cooled to rt then diluted with water. After extracting three times with EtOAc, the organic layers were combined then washed with brine and dried over anhydrous magnesium sulfate. After filtration, the mixture was concentrated under reduced pressure to afford an orange oil 5-bromo-3-nitro-2-(piperidin-1-yl)pyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.30 (1H, d, J=2.3 Hz), 8.22 (1H, d, J=2.2 Hz), 3.39 (4H, d, J=5.7 Hz), 1.75 (6H, m).

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionAfter extracting three times with EtOAc
  3. washthe organic layers were combined then washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b65adad5fb4b4d34b9545c187a62426b
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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