Sodium Iodide → (2-Pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine

HRID 1504166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504166
[I-].[Na+].Br[CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:15]=1.C(N(C(C)C)C(C)C)C>O.CN(C=O)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][N:22]([CH2:23][C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)[CH2:4][CH2:5][CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:15]=1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 60761584(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamine

Produkt 1

HCID 66960900(2-Pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Sodium iodide(1.5 g) was added to a DMF solution (20 ml) of 2-(3-bromopropoxy)tetrahydropyran(0.85 ml). The mixture was stirred at 70° C. for 7 hours. The reaction mixture was cooled to room temperature. (2-Pyridin-3-yl-ethyl)-pyridin-4-ylmethyl-amine (1.28 g), and N-ethyldiisopropylamine(1.3 ml) were added thereto. The mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was washed with water and then saturated saline, and dried with anhydrous sodium sulfate. After condensation under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate: methanol=20:1→4:1). The purified product was condensed under reduced pressure to give the title compound(236 mg) as a colorless oily matter.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with water
  5. dry with materialsaturated saline, and dried with anhydrous sodium sulfate
  6. customAfter condensation under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate: methanol=20:1→4:1)
  8. customcondensed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-95e2df74697f404baf882308f26d521f
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212187B2

Notizen zur Reaktion

Wird geladen…