Hydrochloric Acid → (4-Isopropylphenyl)[(2-methoxy-5-pyridyl)methyl]amine

HRID 218546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218546
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl.C(=O)([O-])O.[Na+]>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 17854296N-(4-isopropylphenyl)-6-methoxypyridine-3-carboxamide

Produkt 1

HCID 21957879(4-Isopropylphenyl)[(2-methoxy-5-pyridyl)methyl]amineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A BH3-THF complex/1M THF solution (6.3 mL) was added to N-(4-isopropylphenyl)-6-methoxypyridine-3-carboxamide (0.76 g), and the mixture was heated under reflux for 4 hr. After cooling the reaction mixture, 1 mol/L hydrochloric acid (15 mL) was added and the mixture was stirred at room temperature for one day. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give (4-isopropylphenyl)[(6-methoxypyridin-3-yl)methyl]amine (0.62 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. additionwas added
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b39c0595e57c498e9e8019b97e0a0805
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198454B2

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