Triethylamine → N-methyl-N-(3,4-dimethoxycinnamyl)-3,4,5-trimethoxyphenylpropiolamide

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Reaction Steps

To the solution of 11.6 g of 3,4,5-trimethoxyphenylpropiolic acid in 60 ml of tetrahydrofuran, 6.0 g of triethylamine are added while stirring, followed by 60 ml of diethyl ether. The mixture is cooled with ice and to the resulting suspension the solution of 5.35 g of ethyl chloroformate in 30 ml of diethyl ether is added dropwise. The mixture is stirred for 15 minutes at 0°-5°, whereupon the solution of 9.7 g of N-methyl-3,4-dimethoxycinnamylamine in 30 ml of diethyl ether is added dropwise, followed by 50 ml of methylene chloride. The mixture is stirred for 30 minutes at room temperature and washed with N hydrochloric acid, 2N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and evaporated under reduced pressure, to yield the N-methyl-N-(3,4-dimethoxycinnamyl)-3,4,5-trimethoxyphenylpropiolamide.

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