Piperidine → 4-Nitro-3-(piperidin-1-yl)pyridine 1-oxide

HRID 69870Notes

Reaction equation

HRID 69870 reaction equation
Br[C:2]1[CH:3]=[N+:4]([O-:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)C>[N+:8]([C:7]1[CH:6]=[CH:5][N+:4]([O-:11])=[CH:3][C:2]=1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 5485213-Bromo-4-nitropyridine N-oxide

Product 1

HCID 147359134-Nitro-3-(piperidin-1-yl)pyridine 1-oxideYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-bromo-4-nitropyridine-N-oxide (1.0 equiv.) and piperidine (2.0 equiv.) in ethanol, at a concentration of 0.2 M, was heated at reflux for 16 hours. Upon cooling the ethanol was removed in vacuo. The residue was partitioned between EtOAc and Na2CO3(sat), and washed further with H2O, NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding 4-nitro-3-(piperidin-1-yl)pyridine 1-oxide (92%). LCMS (m/z): 224.0 (MH+); LC Rt=2.48 min.

Workup

  1. temperatureat reflux for 16 hours
  2. customwas removed in vacuo
  3. customThe residue was partitioned between EtOAc and Na2CO3(sat)
  4. washwashed further with H2O, NaCl(sat.)
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-72bf3e74e91841bfbe73366322a278a1
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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