Triethylamine → Benzeneacetamide, N-(2-(2,3-dihydro-6-methyl-1H-inden-5-yl)ethyl)-3,4-dimethoxy-

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Reaction Steps

5-Aminoethyl-6-methylindan (4.0 g, 0.029 mole) was dissolved in 100 ml of dry benzene, 4 ml of triethylamine was added and a solution of the previously prepared 3,4-dimethoxyphenylacetyl chloride in dry benzene was added to the substituted indan mixture. The reaction mixture was refluxed for several hours and then gently heated overnight at a temperature below reflux. The reaction was then cooled, washed with 3×100 ml of 20% HCl solution, 3×100 ml of 8% NaHCO3 solution and 2×125 ml of water. The benzene layer was then reduced in volume on a rotary evaporator to yield a solid precipitate. The solid was filtered, washed with benzene, air dried to yield a slightly pink powder (3.5 g, mp 144°-145° C.). The crude product was then recrystallized from benzene (large volume), mp 144°-144.5° C.

Provenance & Evidence