2-[(4-Fluorophenoxy)methyl]oxirane → 1-(4-Fluorophenoxy)-3-[2-(2,6-dimethylphenylamino)-ethylamino]-propan-2-ol

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Reaction Steps

3.36 g. 4-Fluorophenyl glycidyl ether are left to stand for 2 days at ambient temperature with 6.6 g. N-(2,6-dimethylphenyl)-ethylenediamine. The reaction mixture is separated by chromatography on silica gel with the elution agent ethyl acetate-methanol-triethylamine (100:10:1 v/v/v) to give, after evaporation of the pure fractions, 5.0 g. of the desired product in the form of a viscous oil. After dissolving in diethyl ether and adding 2.5 g. benzoic acid, the corresponding benzoate precipitates out and is recrystallized from isopropyl alcohol. The desired product is obtained in a yield of 5.2 g. (57% of theory) in the form of colorless crystals; m.p. 105°-106° C.

Provenance & Evidence