Hydrochloric Acid → HCID 19921693, compound

Participants

Reaction Steps

To a mixture of 3-(3-hydroxypropyl)-1H-indole-5-carboxylic acid (4.30 g, 19.63 mmol), triethylamine (3.97 g, 39.26 mmol) and benzylamine (2.10 g, 19.63 mmol) in 150 mL acetonitrile was added 2-chloro-1-methylpyridinium iodide (6.04 g, 23.68 mmol). The mixture was heated to reflux for 16 h. The solution was cooled to room temperature, 70 mL of 0.5N hydrochloric acid added, and the acetonitrile removed in vacuo. The residue was extracted with 250 mL of ethyl acetate. The organic layer was separated and the aqueous layer reextracted with three 50 mL portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (95:5:0.5 CH2Cl2 -MeOH-NH4OH) of the concentrate yielded 3-(3-hydroxypropyl)-N-(phenylmethyl)-1H-indole-5-carboxamide (2.26 g, 37%).

Provenance & Evidence