Water → HCID 68120121, compound

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Reaction Steps

In a system protected by a drying tube and in which a nitrogen atmosphere is maintained, a solution of the product from Step A. (0.80 g., 0.0075 mole) in 25 ml. of absolute ether is added dropwise to a stirred suspension of lithium aluminum hydride (0.19 g., 0.0025 mole) in 15 ml. of absolute ether. After stirring at reflux for 1 hour, the mixture is cooled in ice and hydrolyzed by the successive dropwise addition of water, 0.2 ml., 20% sodium hydroxide, 0.2 ml., and water, 0.6 ml. The granular precipitate is collected and washed thoroughly with ether. The combined etheral filtrate and washings are washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness. The residual oily base is dissolved in absolute ether and treated with a solution of maleic acid (10% excess) in absolute alcohol. The 5-(3-n-butylaminopropyl)-5H-dibenzo[a,d]cycloheptene hydrogen maleate is obtained by dilution of the solution with absolute ether as white neeldes, m.p. 102°-107°C., in a yield of 0.65 g. (60%). Recrystallization from mixtures of isopropyl alcohol-absolute ether and absolute alcohol-absolute ether gives product, m.p. 107.5°-109°C.

Provenance & Evidence