24424-99-5

61468-43-7

497068-73-2

GENERAL STEPS: Example 9 Synthesis of (2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(1-methyl-1,2,3,4-tetrahydro-quinolin-5-yloxy)-propyl]-amine. a) Preparation of tert-butyl 5-hydroxy-3,4-dihydro-2H-quinoline-1-carboxylate: to a stirred 5-hydroxytetrahydroquinoline ( 0.86 g, 5.34 mmol) to a solution of dioxane (25 mL) was added di-tert-butyl dicarbonate (1.16 g, 5.34 mmol). The reaction mixture was stirred at room temperature for 24 hours and then concentrated under vacuum to give an oily product. The crude product was diluted with ether and washed with water. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated to give a thick oily product. Recrystallization by dichloromethane-hexane mixed solvent resulted in 1.25 g of yellow crystal product in 94% yield.