Triethylamine → HCID 10024664, compound

Participants

Reaction Steps

A solution of (2R)-4-bromobenzenesulfonic acid 2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl ester (1.13 g, 2.5 mmol), 3-(5-cyano-1H-indol-3-yl)propylamine (0.65 g, 3.2 mmol) and triethylamine (0.7 mL, 5.0 mmol) in dimethylsulfoxide (40 mL) was heated at 90° C. under nitrogen for 16 hours. The reaction mixture was quenched with 1N sodium hydroxide and extracted with methylene chloride (3×100 mL). The organic layer was washed with water (3×150 mL), dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum. The crude oil was column chromatographed on silica gel (10% methanol-ethyl acetate). The product-containing fractions were concentrated in vacuum to give 0.54 g of the (S)-enantiomer of the title compound as a brown oil. The dihydrochloride salt was prepared in ethyl acetate as a yellow solid, m.p. 170-174° C.

Provenance & Evidence