Triethylamine → 4-(3-Nicotinoylaminopropyloxy)pyridine

HRID 6142

Reaktionsgleichung

Reaktionsgleichung von HRID 6142
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1>C(Cl)Cl>[C:20]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 149941254-(3-Aminopropoxy)pyridine

Produkt 1

HCID 190791674-(3-Nicotinoylaminopropyloxy)pyridineAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 700 mg (4.60 mmol) of 4-(3-aminopropyloxy)pyridine and 1.54 ml (11.0 mmol) of triethylamine in 30 ml of methylene chloride, 830 mg (4.66 mmol) of nicotinoyl chloride hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10 to 1:5) to obtain 1.05 g of the desired compound (yield: 85.8%, colorless crystals).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1.5 hours
  3. washThe reaction mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10 to 1:5)

Quellen und Nachweise

ORD-Eintrag
ord-21c6230f734548bda488fe39bf56a85a
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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