55837-25-7

Fonzylane,Lafon,France,1976

BAN; DCF; MI.

ChEBI: 4-(1-pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-1-butanone is an aromatic ketone.

Introduce 33.6 g (0.2 mol) of 1,3,5-trimethoxybenzene and 100 ml of chlorobenzene into a 500 ml three-neck flask with stirrer, hydrochloric acid bubbler and condenser. Stir to dissolve and add 27.7 g of 4- pyrrolidinobutyronitrile (from 4-chlorobutyronitrile and pyrrolidine). Cool to about 15°-20°C and bubble hydrochloric acid gas in for 4 hours. Cool to about 5°C and add 200 cm3 of water. Stir. Decant the aqueous layer, wash again with 150 cm3 of water. Combine the aqueous layers, drive off the traces of chlorobenzene by distilling 150 cm3 of water, and heat under reflux for one hour. Cool and render alkaline by means of 60 ml of sodium hydroxide solution of 36° Baume. Extract twice with 100 ml of ether. Wash the ether with 100 ml of water. Dry the ether over sodium sulfate and slowly run in 50 ml of 5N hydrogen chloride solution in ether, at the boil. Cool in ice. Filter, wash with ether and dry in a vacuum oven. 33.6 g of crude product are obtained. Recrystallize from 200 ml of isopropanol in the presence of 3 SA carbon black. Filter. Wash and dry in a vacuum oven.
26.9 g of a white, crystalline water-soluble powder are obtained. Yield: 39.2%. Instantaneous melting point: 192°-193°C.

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