Sodium Iodide → 6-Bromo-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinoline

HRID 72564

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:26][C:25]1[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)[CH2:7][CH2:6][CH2:5]2

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a stirred solution of 6-bromo-1,2,3,4-tetrahydro-quinoline (3.00 g, 12.1 mmol) in dimethylformamide (25 mL) was added potassium carbonate (3.3 g, 24.1 mmol), sodium iodide (0.905 g, 6.0 mmol) and 4-methoxybenzyl chloride (2.5 mL, 18.1 mmol) and heated at 50° C. After 18 h, reaction mixture was cooled to room temperature and quenched by the addition of water and extracted with ethyl acetate (2×20 mL). The organic layer was washed with water (2×20 mL), brine (20 mL), dried over sodium sulfate, concentrated and purified by the silica gel column chromatography to furnish 6-bromo-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinoline (2.5 g).

Aufarbeitung

customreaction mixture
temperaturewas cooled to room temperature
customquenched by the addition of water
extractionextracted with ethyl acetate (2×20 mL)
washThe organic layer was washed with water (2×20 mL), brine (20 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated
custompurified by the silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-8bf55cf3f78445708808a4a1910daf74
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08828951B2

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