Piperidine → Piperidine, 5-nitro-2-pyridyl-

HRID 1471011Notes

Reaction equation

HRID 1471011 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 97158Piperidine, 5-nitro-2-pyridyl-Yield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a slurry of 2-chloro-5-nitropyridine (100 g, 632 mmol) in ethanol (2000 mL) at room temperature was added piperidine (206 mL, 2.08 mol) and the mixture heated to 60° C. for 30 minutes. The cooled mixture was concentrated and the residue taken up in CH2Cl2 then washed with saturated NaHCO3 and brine. The mixture was dried (Na2SO4), filtered, and concentrated to provide the title compound as a yellow solid (130.4 g, 99% yield). 1H NMR (400 MHz, DMSO-D6) δ 8.94 (d, J=2.9, 1H), 8.17 (dd, J=9.6, 2.9, 1H), 6.93 (d, J=9.6, 1H), 3.79-3.73 (m, 4H), 1.69-1.64 (m, 2H), 1.61-1.51 (m, 4H).

Workup

  1. concentrationThe cooled mixture was concentrated
  2. washthen washed with saturated NaHCO3 and brine
  3. dry with materialThe mixture was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-52d459864dc645f5af4fab95cf2fd1f2
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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