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

HRID 1837173
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1837173
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

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

Produkt 1

HCID 11174879Ammonium 2-[[1-(4-pyridinyl)piperidin-4-ylmethyl]amino]pyridine-3-carboxylateAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-48495db7c749476f8ce1e3f474fbaad3
Quelldatensatz
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06780878B2

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