2-(5,6-디메톡시-1-인데닐 )에틸 아민의 합성

Synthesis of 2-(5,6-dimethoxy-1-indenyl)ethyl amine

In order to search the new serotonin bioisoster, 2-(5,6-dimethoxy-1-indenyl)ethyl amine(1) was synthesized. 3,4- Dimethoxybenzaldehyde , as starting material, was condensed with masonic acid in the pre sense of pyridine and piperidine to form 3,4- dimethoxycinnamic acid(2). Compound 2 was performed catalytic hydrogenation with 17% Pd-C to give propanoic acid derivative 3, which was cyclized by Friedel-Crafts acylation to afford 5,6-dimethoxyindan-1-one(4). Compound 4 was reduced with NaBH4 in ethanol to obtain 1-indanol 5, and it was dehydrated to give 5,6-dimethoxy-1- indene(6). This compound was lithiate d with 2.5M n-butyllithium and reacted with 1,2-dibromoe thane to give 2- (5,6-dimethoxy-1-indenyl)ethyl bromide(7), and which was treated with anhydrous ammonia to synthesize compound 1.