Piperidine → 3-Nitro-4-piperidin-1-ylpyridine

HRID 1918911Notes

Reaction equation

HRID 1918911 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1Cl)([O-:3])=[O:2].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)C>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 35076693-Nitro-4-piperidin-1-ylpyridineYield 115.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A 500-mL single-neck round-bottomed flask equipped with a reflux condenser and magnetic stirrer was purged with nitrogen and charged with 3-nitro-4-chloro-pyridine (10.0 g, 63.3 mmol), piperidine (16.2 g, 190 mmol) and ethanol (200 mL). After heating at 70° C. for 2 h, the solvent was removed under reduced pressure, and the residue was partitioned between ethyl acetate (200 mL) and 10% aqueous potassium carbonate (100 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 100% yield (15.2 g) of 159a as a yellow oil: 1H NMR (500 MHz, CDCl3) d 8.81 (s, 1H), 8.31 (d, 1H, J=6.0 Hz), 6.86 (d, 1H, J=6.0 Hz), 3.22 (t, 4H, J=4.5 Hz), 1.72 (m, 6H); MS (APCI+) m/z 208.4 (M+H).

Workup

  1. customA 500-mL single-neck round-bottomed flask equipped with a reflux condenser and magnetic stirrer
  2. customwas purged with nitrogen
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate (200 mL) and 10% aqueous potassium carbonate (100 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-69a3f45424674f06a817c7ae631a4340
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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