Potassium Hydroxide → 9,9-Dimethyl-10-[5-methyl-1-(5-methyl-1-pyrrolin-2-YL)-2-pyrrolin-2-YL]acridan

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Reaction Steps

A mixture of 5-methyl-2-pyrrolidinone (2.0 g., 0.02 mole) and phosphorus oxychloride (3.0 g., 0.02 mole) in 15 ml. of 1,2-dichloroethane after standing 15 hr. at room temperature is combined with 9,9-dimethylacridan (2.1 g., 0.01 mole) after a 48 hr. period is added to 30 ml. of 5N potassium hydroxide and 30 g. of crushed ice. The 1,2-dichloroethane fraction is separated, extracted with 50 ml. of 1.5N hydrochloric acid and 50 ml. of water and dried over magnesium sulfate. Concentration of the 1,2-dichloroethane solution provides a residue which is stirred with 100 ml. of ether and filtered. The filter cake containing crude hydrochloride salt of the product is stirred with sodium hydroxide solution affording the free base. Crystallization from n-heptane provides 1.3 g. (35% yield) of 9,9-DIMETHYL-10-[5-METHYL-1-(5-METHYL-1-PYRROLIN-2-YL)-2-PYRROLIN-2-YL]ACRIDAN, m.p. 135°-139° C. from which the hydrochloride salt is prepared according to the procedure of Example 1. Analytically pure 9,9-DIMETHYL-10-[5-METHYL-1-(5-METHYL-1 -PYRROLIN-2-YL)-2-PYRROLIN-2-YL]ACRIDAN HYDROCHLORIDE, from acetone-ether, has a melting point of 247.5°-248.0° C. (corr.).

Provenance & Evidence