Methyl bromoacetate → [4-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-piperazin-1-yl]-acetic Acid Methyl Ester

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Reaction Conditions

Reaction Steps

To a solution of (2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(3-piperazin-1-yl-phenoxy)-propyl]-amine hydrochloride (114 mg, 0.187 mmol—Example 168) in methanol (15 mL) was treated with bromo-acetic acid methyl ester (57 mg, 0.375 mmol) and diisopropyl-ethyl-amine (48 mg, 0.375 mmol). The resulting solution was heated at 50° C. for 3 hours, cooled to room temperature, and concentrated. The crude material was dissolved in EtOAc and washed with water (1×). The organic layer was then washed with brine (1×), dried over sodium sulfate, and filtered. The EtOAc was concentrated and the sample was dried under vacuum to title compound as an oil (99 mg, 78%). MS(ES) m/e 622.2 ([M−COOCH3]+).

Provenance & Evidence