Piperidine → 2-Nitro-5-(piperidin-1-yl)pyridine

HRID 586522Notes

Reaction equation

HRID 586522 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.C(OCC)(=O)C>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 29279612-Nitro-5-(piperidin-1-yl)pyridineYield 85.7%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-nitropyridine (5.6 g, 27.6 mmol), tetra-n-butyl ammonium iodide (0.510 g, 1.38 mmol), piperidine (2.58 g, 30.3 mmol) and potassium carbonate (3.85 g, 30.3 mmol) were mixed in DMSO (50 mL). The reaction mixture was warmed to 80° C. for 4 hours. The reaction mixture was diluted with ethyl acetate and filtered. The volume was reduced to remove ethyl acetate, the remaining solution was diluted with water (50 mL). A precipitate immediately formed and was collected by filtration and washed on the funnel with water to provide 6′-nitro-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl as an orange-brown solid (4.90 g, 85.7%). 1H NMR δ (400 MHz, CDCl3) 7.76 (s, 1H), 7.15 (d, J=7.3 Hz, 1H), 6.49 (d, J=8.5 Hz, 1H), 3.84 (m, 5H), 3.00 (m, 4H), 2.60 (s, 1H).

Workup

  1. filtrationfiltered
  2. customto remove ethyl acetate
  3. additionthe remaining solution was diluted with water (50 mL)
  4. customA precipitate immediately formed
  5. filtrationwas collected by filtration
  6. washwashed on the funnel with water

Sources & evidence

ORD record
ord-6ec612f1f50d4e6790303dd59a34df2f
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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