Potassium Iodide → N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylprop yl]-4-pyrrolidin-1-ylmethylbenzamide hydrochloride

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Reaction Steps

Compound 70 (2.25 g, 71%) was produced as an oily product from 4-chloromethylbenzoic acid (1.23 g, 7.2 mmol), the compound produced in Example 17 (2.48 g, 6.0 mmol), triethylamine (0.83 mL, 6.0 mmol), WSC.HCl (1.38 g, 7.2 mmol) and CH2Cl2 (20 mL) according to the same manner as Example 30. Compound 70 (1.06 g, 2.0 mmol), pyrrolidine (0.25 mL, 3.0 mmol), potassium carbonate (0.55 g, 4.0 mmol) and potassium iodide (0.1 g) were added to DMF (15 mL) and the mixture was stirred for 20 hours at room temperature. Water was added to the reaction mixture followed by extracting with ethyl acetate. The organic layers were combined, washed with water and a saturated saline solution and dried over anhydrous sodium sulfate. The residual oily product produced by evaporation of the solvent therefrom in vacuo was crystallized from petroleum ether to give Compound 64 (1.12 g, 93%).

Provenance & Evidence