Hydrochloric Acid → (s)-n,n-Dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine-hydrochloride

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Reaction Conditions

Reaction Steps

Diisopropylethylamine (210 ml) is added to a solution of (S)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)-propanamine (311 g; 99.6% ee) in toluene (1200 ml) and then phenylchloroformate (150 ml) is added at 60° C. After stirring at 80° C. for two hours, the mixture is cooled down, shaken with a diluted solution of hydrochloric acid, water and a 2% solution of sodium hydrogencarbonate. The organic phase is dried with sodium sulfate and evaporated. The evaporation residue is dissolved in ethanol (300 ml) and a 5M solution of potassium hydroxide (400 ml) is added drop by drop under reflux. After refluxing for two hours, the mixture is evaporated to half the volume, diluted with water (1,000 ml) and extracted with toluene (300 ml). The organic phase is dried with sodium sulfate and evaporated. The evaporation residue is dissolved in ethanol (300 ml), ammonium chloride is added (80 g) and the mixture is refluxed for two hours. The mixture is then evaporated to dryness, toluene (1,000 ml) is added, and the mixture is filtered while hot. After cooling to lab temperature, the precipitated light-brownish crystals are sucked off. The yield is 183 g (55%), b.p. 167-169° C.

Provenance & Evidence