2-Chloro-5-nitropyridine → HCID 57461794, compound

HRID 1020346Notes

Reaction equation

HRID 1020346 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[OH:20][C:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CCO.CCOC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:24]2[CH2:25][CH2:26][C:21]([OH:20])([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:22][CH2:23]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 81531DiisopropylethylamineHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 57461794HCID 57461794, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (0.9 g) in EtOH (5 mL) was added N,N-diisopropylethylamine (2.9 mL) and 4-hydroxy-4-phenylpiperidine (1.5 g). The reaction mixture was heated at 140° C. for 20 min by microwave. Then the reaction mixture was cooled to RT, diluted with EtOAc (150 mL), washed with H2O (2×100 mL), saturated NH4Cl (3×100 mL), brine (1×100 mL), dried over Na2SO4, filtered, and concentrated to give B-1.

Workup

  1. temperatureThen the reaction mixture was cooled to RT
  2. washwashed with H2O (2×100 mL), saturated NH4Cl (3×100 mL), brine (1×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give B-1

Sources & evidence

ORD record
ord-e7830717b42c47f090456c867faf199c
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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