4-(1,3-Benzodioxol-5-yl)-2-butanone → N-[4-(3,4-methylenedioxyphenyl)-but-2-yl]-beta-(3,4-dihydroxyphenyl) ethylamine hydrochloride

Participants

Reaction Steps

In 10 ml. of a saturated solution of sodium bicarbonate is dissolved 1.0 g. (0.00526 mole) dopamine hydrochloride. A solution of 4-[3,4-(methylenedioxy) phenyl]butan-2-one (1.10 g., 0.00526 mole) in 10 ml. ethanol is added to the above sodium bicarbonate solution. A white precipitate develops. The slurry is charged with 0.1 g. platinum oxide and hydrogenated for three hours at 20 psi. The solids are filtered and the solution concentrated. The residue is triturated with ethanol, refiltered and again concentrated. The oily residue is treated with ethereal hydrochloric acid and the so-formed solids collected and crystallized from methanol-isopropanol to give N-[4-(3,4-methylenedioxyphenyl)-but-2-yl]-β-(3,4-dihydroxyphenyl) ethylamine hydrochloride as a white solid, m.p. 204°-206°.

Provenance & Evidence