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

HRID 1183075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183075
[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>C(OCC)(=O)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

8

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]amineAusbeute 13,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Sodium iodide (1.5 g, 10 mmol) was added to a DMF solution (20 ml) of 2-(3-bromopropoxy)tetrahydropyran (0.85 ml, 5 mmol), and stirred at 70° C. for 7 hours. The reaction mixture was cooled to room temperature. (2-Pyridin-3-ylethyl)pyridin-4-ylmethylamine (1.28 g, 6 mmol) and N-ethyl diisopropylamine (1.3 ml, 7.5 mmol) were then added to the reaction mixture and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with water, and a saturated sodium chloride aqueous solution, in this order. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→4:1). The purified product was concentrated under reduced pressure to thereby obtain 236 mg (yield: 13%) of (2-pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred at room temperature overnight
  3. washThe organic layer was washed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→4:1)
  7. concentrationThe purified product was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2ed7549bc79f46188664388de101022f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664217B2

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