Triethylamine → HCID 13487103, compound

Participants

Reaction Steps

Propionylchloride (0.28 g, 0.0030 mol) in dry ether (5 ml) was slowly added at 5° C. to a solution of (-)-cis-5-methoxy-1-methyl-2-(n-propylamino)tetralin (0.35 g, 0.0015 mol), triethylamine (0.31 g, 0.0030 mol) and dry ether (45 ml). The mixture was stirred at room temperature for 1 hour, whereupon the triethylammoniumchloride formed was filtered off and the solvent evaporated. The residue (0.40 g) dissolved in dry tetrahydrofuran (10 ml) was added to a suspension of LiAlH4 (0.80 g, 0.021 mol) in dry tetrahydrofuran (40 ml) under nitrogen. After stirring under reflux for 5 hours, the mixture was hydrolyzed, the precipitate was filtered off, and the solvent was evaporated. The residue was passed through an alumina column with ether/light petroleum (20:80) as eluant, and the amine was precipitated as the hydrochloride and recrystallized from ethanol-ether to give (-)-cis-5-methoxy-1-methyl-2-(di-n-propylamino)tetralin hydrochloride. (0.37 g, 79%) m.p. 161°-162° C. [α]D22 =-48.2 (c=1.1, CH3OH).

Provenance & Evidence