Triethylamine → 1-(2H-1,3-Benzodioxol-5-yl)pyrrolidin-2-one

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Reaction Steps

4-Chlorobutyryl chloride (1095.5 g, 7.77 mole) was added at 10°-25° C. to a mixture of 3,4-(methylenedioxy)aniline (1000.0 g, 7.29 mole), triethylamine (749.0 g, 7.40 mole) and methylene chloride (25000 mL). After stirring for 18 hours at ambient temperature ether was added and the butyramide intermediate was filtered then reslurried in water. The damp butyramide was combined with methylene chloride (10 L), 50% w/w aqueous sodium hydroxide (2000.0 g, 25.0 mole) and benzyltriethylammonium chloride (50.0 g, 0.22 mole). After stirring for 2.5 hours at ambient temperature the mixture was diluted with water and the aqueous layer was then separated. The methylene chloride layer was washed with water, decolorized with Darco G-60 and Filtrol #19, then vacuum concentrated. Ether was added to the concentrate. The mixture was chilled and the solids were collected and recrystallized from methylene chloride/ether giving 2245.0 g (75), m.p. 89°-91° which was one spot on tlc analysis.

Provenance & Evidence