2-Chloro-5-nitropyridine → 1-(5-nitropyridin-2-yl)piperidin-4-ol

HRID 2079599Notes

Reaction equation

HRID 2079599 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[OH:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C(O)CC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:16][CH2:17][CH:12]([OH:11])[CH2:13][CH2:14]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 79341Piperidin-4-ol

Product 1

HCID 28597681-(5-nitropyridin-2-yl)piperidin-4-olYield 97.4%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 11.0 g (6.3 mmol) of 2-chloro-5-nitropyridine in 20 mL of n-propanol was added 1.9 g (18.9 mmol) of 4-hydroxypiperidine, and the mixture was stirred for 1.5 hours at 100° C. After cooling the reaction mixture, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:dichloromethane/methanol=50/1) to give 1.37 g (97%) of the title compound.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluent:dichloromethane/methanol=50/1)

Sources & evidence

ORD record
ord-31e9e8e29d0444ba9ad244106dce8f71
Source dataset
uspto-grants-2011_04
Patent number
US07932250B2

Reaction notes

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