Methanol → HCID 21502282, compound

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Reaction Steps

This enamine product is then hydrolyzed by refluxing with stirring in 150 ml. 10% in water and 75 ml. of methanol. The methanol is then removed by evaporation of the reaction mixture on a rotary evaporator. The residual material containing the desired product is made alkaline by adding solid NaHCO3 until no more CO2 is evolved. The residue is then extracted with toluene and ether. The combined extracts containing the product are dried over anhydrous MgSO4, filtered, and the solvents removed with a rotary evaporator. There remains a dark brown residual oil which when seeded crystallizes slowly. This product is collected and recrystallized from hexane two times to give 1-methyl-4-(10,11-dihydro-10-oxo-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, m.p. 138°-140°C. Three more recrystallizations from hexane gives product, m.p. 141°-142°C.

Provenance & Evidence