Potassium Hydroxide → N-(3-Bromo-5-methylbenzyl)-N-methyl-[4-(1-methyl-1-phenylethyl)benzyl]amine

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Reaction Steps

N-(3-bromo-5-methylbenzyl)methylamine hydrochloride (11.0 g) was dissolved in methanol (30 ml), and potassium hydroxide (800 mg) was added thereto. The mixture was stirred until complete dissolution was effected, and 4-(1-methyl-1-phenylethyl)benzaldehyde (8.96 g) was added thereto. The mixture was stirred for 15 minutes, and sodium cyanoborohydride (950 mg) in methanol (10 ml) was added dropwise. The mixture was stirred for 30 minutes, and insoluble matter was filtered off, followed by washing with methanol. The filtrate was concentrated under reduced pressure, and water was added thereto, followed by extraction with ether (250 ml). 1N Hydrochloric acid (150 ml) was added to the organic layer, and the mixture was stirred. Crystals that precipitated were collected by filtration, and washed with water and then with ether. The filtrate was separated, and the aqueous layer was combined with the above crystals. The mixture was alkalinized with sodium hydroxide, and extracted with chloroform (250 ml), followed by drying over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=30:1), to thereby yield 7.60 g of the target compound (yield: 45.0%).

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