Hydrochloric Acid → N-(2-(5-(4-(4-Chlorophenoxy)piperidine-1-carbonyl)-1H-indol-1-yl)ethyl)acetamide

Participants

Reaction Steps

To a stirred solution of (1-(2-aminoethyl)-1H-indol-5-yl)(4-(4-chlorophenoxy)piperidin-1-yl)methanone (30 mg, 0.075 mmol, Example 385) and pyridine (1 mL) was added acetic anhydride (0.0085 mL, 0.090 mmol) at room temperature. After stirring at room temperature for 2 hours, the mixture was poured into 1M aqueous hydrochloric acid solution (5 mL). This was extracted with ethyl acetate (5 mL) and washed with saturated sodium hydrogen carbonate aqueous solution (5 mL) and brine (5 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) and then preparative LC-MS to give 8.9 mg (27% yield) of the title compound.

Provenance & Evidence