4-Piperidinecarboxamide → 1-(5-Nitropyridin-2-yl)piperidine-4-carboxamide

HRID 1691895Notes

Reaction equation

HRID 1691895 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](Cl)=[N:8][CH:9]=1)([O-:3])=[O:2].[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]([NH2:19])=[O:18])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([NH2:19])=[O:18])[CH2:13][CH2:12]2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 31651361-(5-Nitropyridin-2-yl)piperidine-4-carboxamideYield 112%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-nitro-2-chloro-pyridine (2 g, 12.6 mmol), piperidine-4-carboxylic acid amide (1.78 g, 13.9 mmol), and potassium carbonate (3.48 g, 25.2 mmol) in anhydrous 1,4 dioxane (65 mL) was heated in an oil bath at 100° C. for 5 hr. The reaction was diluted with water (500 mL) and extracted with ethyl acetate (500 mL). The resulting yellow precipitate that form in both layers was filtered off and washed with minimal ethyl acetate, dichloromethane, and hexanes, and dried. The aqueous layer was extracted with dichloromethane (three times with 200 mL each). This dichloromethane layer was washed with brine, combined with the original ethyl acetate extract dried over sodium sulfate, and concentrated to a yellow solid. The yellow solid and the original yellow filtered precipitate were combined to give 5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid amide (2.93 g, 112%) as a yellow solid. LCMS calcd for C11H14N4O3 (m/e) 250, obsd 251 (M+H).

Workup

  1. extractionextracted with ethyl acetate (500 mL)
  2. filtrationThe resulting yellow precipitate that form in both layers was filtered off
  3. washwashed with minimal ethyl acetate, dichloromethane, and hexanes
  4. customdried
  5. extractionThe aqueous layer was extracted with dichloromethane (three times with 200 mL each)
  6. washThis dichloromethane layer was washed with brine
  7. extractionextract
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-9a72e0435dd24c4eb0f23ac3eaf4133d
Source dataset
uspto-grants-2012_04
Patent number
US08153644B2

Reaction notes

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