1,2,3,4-Tetrahydroquinoline → HCID 10309434, compound

Participants

Reaction Steps

A solution of 1-Bromo-3-isocyanato-propane (0.164 g, 1.0 mmol) in acetonitrile is stirred with 1,2,3,4-Tetrahydro-quinoline (0.133 g, 1.0 mmol) and diisopropylethylamine (0.2 ml, 1.2 mmol). The reaction mixture is stirred for 2 hours at ambient temperature and then the solvent removed. The crude product is taken-up in acetonitrile (4 ml) and diisopropylethylamine (0.2 ml, 1.2 mmol) and 3-(4-Fluoro-phenoxy)-azetidine hydrochloride (0.11 g, 1.0 mmol) added. The reaction mixture is stirred at ambient temperature for 18 hours, the solvent evaporated and the crude partitioned between ethylacetate and saturated sodium bicarbonate solution. The organic phase is washed with brine, dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (elution gradient ethylacetate then 5:95 methanol/dichloromethane) to afford 3,4-Dihydro-2H-quinoline-1-carboxylic acid {3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-amide. [MH]+ 444.2

Provenance & Evidence