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In order to search the new serotonin bioisoster, 2-(5,6-dimethoxy-l-indenyl)ethyl amine(1) was synthesized. 3,4-Dimethoxybenzaldehyde, as starting material, was condensed with malonic acid in the presence of pyridine and piperidine to form 3,4-dimethoxycinnamic acid(2). Compound 2 was performed catalytic hydrogenation with 10％ Pd-C to give propanoic acid derivative 3, which was cyclized by Friedel-Crafts acylation to afford 5,6-dimethoxyindan-l-one(4). Compound 4 was reduced with NaBH$_4$ in ethanol to obtain l-indanol 5, and it was dehydrated to give 5,6-dimethoxy-l-indene(6). This compound was lithiated with 2.5M n-butyllithium and reacted with 1,2-dibromoethane to give 2-(5,6-dimethoxy-l-indenyl)ethyl bromide(7), and which was treated with anhydrous ammonia to synthesize compound 1.
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