Water → 2-[3-(4-Fluorophenyl)-propyl]-6-allyloxy-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 257043

Reaktionsgleichung

Reaktionsgleichung von HRID 257043
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][CH2:9][CH2:8]2)[CH:2]=[CH2:3].Br[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1.[H-].[Na+].O>CN(C)C=O>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][CH2:17][N:10]2[CH2:9][CH2:8][C:7]3[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[CH:6]=3)[C:11]2=[O:15])=[CH:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 147371331-(3-Bromopropyl)-4-fluorobenzeneHCID 189639526-Allyloxy-1,2,3,4-tetrahydroisoquinolin-1-one

Produkt 1

HCID 189639302-[3-(4-Fluorophenyl)-propyl]-6-allyloxy-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-allyloxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (10.6 g, 52 mmol) and 1-bromo-3-(4-fluorophenyl)-propane (17 g, 78 mmol) and KI (430 mg, 2.6 mmol) in dimethyl formamide (DMF) (125 mL) is added NaH (3.1 g, 78 mmol). After 4 hours the reaction mixture is poured into H2O (500 mL) and the resulting suspension is extracted with EtOAc (3×300 mL). The combined organic extracts are washed with H2O (5×200 mL), saturated NaCl solution (2×200 mL), dried over MgSO4 and concentrated in vacuo. The residue is chromatographed (silica gel, 1:1 EtOAc/hexane) to yield 2-[3-(4-fluorophenyl)-propyl]-6-allyloxy-1-oxo-1,2,3,4-tetrahydroisoquinoline as a brown oil.

Aufarbeitung

  1. extractionthe resulting suspension is extracted with EtOAc (3×300 mL)
  2. washThe combined organic extracts are washed with H2O (5×200 mL), saturated NaCl solution (2×200 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed (silica gel, 1:1 EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-352cb185a94147559b750cc1632d8a6a
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260316

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