FIELD: chemistry.
SUBSTANCE: invention relates to an improved method of producing 2-(N, N-dialkylaminomethyl) styrenes of general formula: where R1= R2= Et; R1=R2=Me; R1=Me, R2=Et; R1=Me, R2=Bn; R1=Me, R2=n-Bu; R1=Me, R2=i-Pr; R1=Et, R2=i-Pr; R1=Et, R2=Bn or R1=Et, R2=n-Bu. Method consists in fact that isoquinoline is subjected to react with alkyl halide or dialkyl sulphate to produce respective isoquinoline salt. Latter should be reduced in presence of formic acid and triethylamine to obtain N-alkyl-1, 2, 3, 4-tetrahydroisoquinoline which again reacted with alkyl halide or dialkyl sulphate to produce the respective tetrahydroisoquinoline salt. Latter is split by Hofmann reaction under action of alkali. Alkyl halide preferably selected from benzyl chloride, 1-bromo butane or 2-iodide propane and dialkyl sulphate is from ethyl sulphate or dimethyl sulphate. Invention allows improve effectiveness of the process of producing 2-(N, N-dialkylaminomethyl) styrenes and takes place in mild conditions, which do not require complex equipment, inert atmosphere, expensive and toxic reagents.
EFFECT: method increases output of target products to 75-88 % with respect to the initial isoquinoline.
3 cl, 9 ex
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Authors
Dates
2016-03-27—Published
2015-03-04—Filed