Potassium Carbonate → Ammonium 2-[[1-(4-pyridinyl)piperidin-4-ylmethyl]amino]pyridine-3-carboxylate

HRID 49850Notes

Reaction equation

HRID 49850 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][NH2:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CO>[N:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][NH:24][C:2]3[C:3]([C:4]([O-:6])=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=3)[CH2:21][CH2:22]2)=[CH:13][CH:12]=1.[NH4+:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acidHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine

Product 1

HCID 11174879Ammonium 2-[[1-(4-pyridinyl)piperidin-4-ylmethyl]amino]pyridine-3-carboxylateYield 96.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloronicotinic acid (10.74 g, 67.5 mmol), 1-(4-pyridyl)piperidine-4-methylamine (8.60 g, 45.0 mmol), and potassium carbonate 15.5 g. 112.6 mmol) in dimethylformamide (90 mL) was heated at reflux. After 16 h. the mixture was diluted with methanol, filtered, and concentrated. The residue was dissolved in methanol, acidified with 1 N HCl in ether, heated at reflux for 0.25 h, cooled, and the solid removed by filtration. The filtrate was then treated with 2 M NH3 in methanol until slightly basic, triturated with THF and the resulting solid collected by filtration yielding 10.75 g of the title compound which was used without further purification.

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in methanol
  5. temperatureheated
  6. temperatureat reflux for 0.25 h
  7. temperaturecooled
  8. customthe solid removed by filtration
  9. additionThe filtrate was then treated with 2 M NH3 in methanol until slightly basic,
  10. customtriturated with THF
  11. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-05338da35ad54c0d8ff46c9b5b001544
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Reaction notes

Loading…