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

HRID 2084314Notes

Reaction equation

HRID 2084314 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+]>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

5

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 1

HCID 887MethanolSolvent

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

Sources & evidence

ORD record
ord-2abff89ff19344c4a9038deada0b5070
Source dataset
uspto-grants-2004_04
Patent number
US06716855B2

Reaction notes

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