2-Chloro-3-nitropyridine → HCID 67342130, compound

HRID 1846622Notes

Reaction equation

HRID 1846622 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:13][CH2:12]1>C(#N)C.[Pd]>[N:19]1([CH2:18][CH2:17][CH:14]2[CH2:15][CH2:16][N:11]([C:2]3[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:12][CH2:13]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 2962921-[2-(Piperidin-4-yl)ethyl]piperidine

Product 1

HCID 67342130HCID 67342130, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.317 g (2.00 mmol) of 2-chloro-3-nitro-pyridine in acetonitrile (10 mL) is added 0.393 g (2.00 mmol) of 1-(2-piperdin-4-yl-ethyl)-piperidine. The mixture is heated to 80° C. and stirred overnight. The mixture is cooled to room temperature and concentrated under reduced pressure. The crude residue is dissolved in ethanol (10 mL) and treated with 0.050 g (0.05 mmol) of 10% palladium on carbon. The mixture is placed under an atmosphere of hydrogen and stirred overnight at room temperature. The mixture is concentrated under reduced pressure to provide 0.577 g (quant.) of 4-(2-piperidin-1-yl-ethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-ylamine.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude residue is dissolved in ethanol (10 mL)
  4. stirringstirred overnight at room temperature
  5. concentrationThe mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-865d2017879d41cca1f6e8e6ea0fb29a
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

Loading…