Toluene → HCID 58381033, Verbindung

Beteiligte Stoffe

Reaktionsschritte

4-(1-Amino-1-phenyl-ethyl)-cyclohexanol (30, 404 mg, 1.6 mmol) was evaporated twice to dryness from toluene. The residue was dissolved in dimethylacetamide (3 mL) and the solution added dropwise to a suspension of sodium hydride (114 mg, 4.1 mmol, 60% in mineral oil) in dimethyl acetamide (8 mL) under argon. After stirring for 1 hour, a solution of 1-benzyloxy-7-chloro-6-fluoroquinoline (38, 0.31 g, 1.09 mmol) in dimethylacetamide (6 mL) was added dropwise and the mixture stirred overnight. Then mixture was then heated and stirred at 60° C. for 1 hour before cooling and addition of water (30 mL) to quench the reaction. The product was isolated by extraction with dichloromethane/isopropanol (3:1) and evaporation of the organic phase under reduced pressure. Purification by column chromatography (silica gel, 2% methanol in dichloromethane) gave the desired product (67 mg) as a colourless solid. Rt=4.3 min (Method 3). Detected mass: 487.3 (M+H+).

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