1-Butanol → Benzeneethanamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dimethoxy-

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Reaction Conditions

Reaction Steps

37.7 g of sodium borohydride are suspended in 1500 cc of anhydrous tetrahydrofuran in an inert atmosphere of nitrogen. To the suspension are added 36 g of amide prepared in part (b), while the mixture is stirred and cooled to 10° C., and there is added also 58 cc of glacial acetic acid. The mixture is warmed under reflux for four hours. At the end of this period, the solvent is evaporated under reduced pressure and the residue is treated with water and then with dilute hydrochloric acid to a full acidity. To the mixture is then added a solution of sodium hydroxide until the pH is alkaline and the material is extracted four times with 300 cc each time of dichloromethane. The organic phase is extracted with dilute hydrochloric acid, the acetic solution is washed with dichloromethane. It is then cooled and made alkaline with potassium carbonate and finally extracted again with four portions of dichloromethane, using 200 cc each time. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated. The residue is the crude amine which is recrystallized from ethanol thus giving a pure product, 28.5 g, yield 75%; m.p. 56°-58° C. A single spot is obtained on T.L.C. (eluent: n-butanol, ethanol, acetic acid, water 60:20:40:10).

Provenance & Evidence