Synthesis Of 1-(3', 4'-methylenedioxyphenyl)-2-pyrroliodion-1-phentanone Hydrochloride

1-(3',4'-Methylenedioxyphenyl)-2-pyrrolidino-1-pentanone with hydrochloride is a kind of novel antidepressant. It has outstanding advantages of high potency and continuous drug action. 1-(3',4'-Methylenedioxyphenyl)-2-pyrrolidino-l-pentanone is syhthesized via Friedel-Crafts acylation reaction, carbonyl group's a-bromination and pyrrolidine's nucleophilic substitue from 1,2-(methylenedioxy)benzene, with the total yield of 74.3%.1,2-(methylenedioxy)benzene reacted with valeryl chloride in the presence of kinds of catalysts. The results showed: metallic oxides were less inferior than metallic chloride. When dichloromethane was the reaction solvent, the ratio of 1,2-(methylenedioxy)benzene:valeryl chloride:FeCl3 was 1:1.15:1.1, the reaction temperature was 5℃for 5 h. The 1,2-(methylenedioxy)benzene was about 99.1% conversion, the selectivity of 1-(3,4-methylenedioxyphenyl)-1-one in the products was 88.0%.The reaction feature brominated by different agents was evaluated in detail. The results showed that the yield of 1-(3,4-methylenedioxyphenyl)-2-bromo-1-one was 94.6% when 1-(3,4-Methylenedioxyphenyl)-1-one/bromine molar ratio was 1:1, dropwise time of bromine was 0.5 h, the reaction temperature was 5℃for 5 h.Under the selected conditions:1-(3,4-methylenedioxyphenyl)-2-bromo-1-one, pyrrolidine, sodium hydroxide reacted under room temperature for 5 h with their molar ratio was 1:2:1, the aminate which wasn't purificationed was acidulated directly to the aim product 1-(3',4'-Methylenedioxyphenyl)-2-pyrrolidino-l-pentanone with hydrochloric acid. Its yield was 90.4%.