Hydrochloric Acid → HCID 20308944, compound

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Reaction Steps

4.90 g (0.015 mole) of α-benzylamino-benzylidenephthalide (R = C6H5 ; R' = H; R" =C6H5CH2 ; X = H) is dissolved in 40 ml of absolute dioxane, and dry hydrogen chloride is bubbled through the solution. 10 to 15 minutes of this procedure causes the dioxane solution to grow turbid, with fine crystals precipitating out. 2.84 g (0.075 mole) of sodium boron hydride is added to this suspension. The solution is maintained at room temperature for 2 days, after which the excess of the reducing agent is decomposed with weak hydrochloric acid, the acid solution is diluted with a triple amount of water, neutralized with alkali hydroxide and extracted with ether. The ether extract is dried over magnesium sulfate, filtered off and saturated with dry hydrogen chloride. The resultant white precipitate is filtered off to yield 3.60 g (65%) of 1-benzylamino-1-phthalidyl-1-phenylmethane chloride. Crystallization from absolute methanol with absolute ether added yields 3.10 g (56% of the theoretical) of a product with a melting point of 255° to 257° C.

Provenance & Evidence