Ethanol → Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate

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Reaction Conditions

Reaction Steps

4-Chlorophenylhydrazine hydrochloride, ethyl 3-bromopropionate and triethylamine in ethanol were stirred at 25° C. for 1 h after which the contents were heated at 90° C. for 3 h. The contents were cooled to 25° C. and evaporated to dryness. The residue was acidified with ethanolic HCl and the volatiles were removed under reduced pressure. Ethanol was added followed by N-methyl-4-piperidone hydrochloride. Heating was continued at 90° C. for 16 h. The contents were concentrated in vacuo, basified by adding saturated aqueous NaHCO3, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by chromatography on neutral alumina using methanol-dichloromethane gradient to obtain ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate.

Provenance & Evidence