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

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.

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

ORD record

ord-48495db7c749476f8ce1e3f474fbaad3

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06780878B2