Triethylamine → 3-Nitro-n-[1-(4-pyridyl)piperidin-4-ylmethyl]pyridine-2-amine

HRID 49839Notes

Reaction equation

HRID 49839 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][CH:27]([CH2:30][NH2:31])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1>CCO>[N+:8]([C:7]1[C:2]([NH:31][CH2:30][CH:27]2[CH2:26][CH2:25][N:24]([C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[CH2:29][CH2:28]2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine

Product 1

HCID 234977553-Nitro-n-[1-(4-pyridyl)piperidin-4-ylmethyl]pyridine-2-amineYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-3-nitropyridine (290 mg, 1.83 mmol), triethylamine (0.26 mL) and 1-(4-pyridyl)-piperidine-4-methylamine (350 mg, 1.83 mmol) in EtOH (10 mL) was heated at reflux. After 17 h, the mixture was concentrated and the residue was purified by chromatography (SiO2, 2 to 4% (2 N NH3 in methanol) in chloroform) yielding 340 mg (60%) of the title compound.

Workup

  1. temperatureat reflux
  2. concentrationthe mixture was concentrated
  3. customthe residue was purified by chromatography (SiO2, 2 to 4% (2 N NH3 in methanol) in chloroform)

Sources & evidence

ORD record
ord-665127de5f8643a696f7c88b4a06e24c
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Reaction notes

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