Triethylamine → Ammonia

Participants

Reaction Steps

To a solution of 3-[3-(1-pyrrolidinylmethyl)phenoxy]propylamine (0.7 g) and triethylamine (0.4 g) dissolved in dry dimethylformamide (5 ml) is added in dropwise fashion succinyl chloride (0.17 ml) at -10° C., and then the reaction mixture is slowly warmed up to room temperature, and stirred for 4 hours. The solvent is removed under reduced pressure, and the residue is distributed to ethyl acetate and saturated sodium hydrogencarbonate solution, and the organic layer is separated, dried on anhydrous sodium, sulfate and evaporated. The residue is chromatographed on a column of silica gel, the fractions eluted with methanol are removed, and the fractions eluted with methanol-conc. aqueous ammonia (50:1 (V/V)) solution give the titled compound (0.55 g) as an oily material. The oily material thus obtained is dissolved in ethanol, and a solution of oxalic acid (0.2 g) in ethanol is added. White crystals precipitated are collected by filtration and further recrystallized from an aqueous ethanol to give the oxalate of the titled compound. mp 157°-159° C.

Provenance & Evidence