(4-Bromophenyl)(2-fluoro-4-((6-(methyl-2-propen-1-ylamino)hexyl)oxy)phenyl)methanone → HCID 18434102, compound

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Reaction Steps

Analogously to Example 33, 17.55 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl]-(4-bromo-phenyl)-methanone are boiled under reflux for 23 hrs. with 50.7 ml of 4-methoxybenzylamine and 6.5 g of potassium carbonate in 600 ml of toluene. After filtration, evaporation and purification over silica gel with methylene chloride/methanol (2.5% to 10%) there are obtained 17.43 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-(4-methoxy-benzylamino)-phenyl]-(4-bromo-phenyl)-methanone. A solution of this material in 200 ml of trifluoroacetic acid is stirred at room temperature for 45 hrs., evaporated and the residue is converted into the free base with methylene chloride/saturated sodium bicarbonate solution. After purification over silica gel with methylene chloride/methanol (9:1) there are obtained 13.23 g of [2-amino-4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl]-(4-bromo-phenyl)-methanone. 9.1 g of the free base are dissolved in methylene chloride/ether and converted with 2.25 g of fumaric acid and by stirring overnight into 7.28 g of [2-amino-4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl]-(4-bromo-phenyl)-methanone•fumarate (1:1), m.p. 78° C. (with decomposition).

Provenance & Evidence