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

HRID 73508Notes

Reaction equation

HRID 73508 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)C>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 35076693-Nitro-4-piperidin-1-ylpyridineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4-chloro-3-nitropyridine (1.0 equiv.) and piperidine (2.0 equiv.) in ethanol, at a concentration of 0.5 M, was stirred at rt for 48 hours at which time the ethanol was removed in vacuo. The residue was partitioned between EtOAc (300 mL) and Na2CO3(sat.) (75 mL), was washed further with H2O (50 mL), NaCl(sat.) (50 mL), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding 3-nitro-4-(piperidin-1-yl)pyridine (95%). LCMS (m/z): 207.7 (MH+); LC Rt=1.60 min. 1H NMR (CDCl3): δ 8.80 (s, 1H), 8.31 (d, J=5.7, 1H), 6.84 (d, J=6.3, 1H), 3.18-3.21 (m, 4H), 1.64-1.78 (m, 6H).

Workup

  1. customwas removed in vacuo
  2. customThe residue was partitioned between EtOAc (300 mL) and Na2CO3(sat.) (75 mL)
  3. washwas washed further with H2O (50 mL), NaCl(sat.) (50 mL)
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-ff5d446faade4fd78eaf6c0ea817cbf4
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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