Methyl iodide → HCID 66650277, compound

Participants

Reaction Steps

NaH (60% in mineral oil, 30 mg, 0.74 mmol) was added to a solution of 4-[benzyl-(1H-indol-5-yl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 0.37 mmol) in DMF (1.0 mL). The reaction mixture was stirred for 1 hour and then methyliodide (0.06 mL, 0.93 mmol) was added. The resulting mixture was stirred for 2 hours and it was then quenched by addition of a saturated aqueous solution of NH4Cl. The organic layer was separated and the aqueous layer was extracted twice with EtOAc (20 mL); the combined organic extracts were washed with brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure to give a yellow foam. This residue was dissolved in DCM (5 mL) and trifluoroacetic acid (0.29 mL, 3.7 mmol) was added. The resulting mixture was stirred at room temperature for 16 hours; it was then evaporated under reduced pressure and the residue was purified by flash chromatography (0% to 20% of MeOH in DCM) to give 115 mg (97% yield) of benzyl-(1-methyl-1H-indol-5-yl)-piperidin-4-yl-amine trifluoroacetate, MS=320 [M+H]+.

Provenance & Evidence