Hydrochloric Acid → HCID 86699302, compound

Participants

Reaction Conditions

Reaction Steps

A 40 mL reaction vial was charged with 238e (0.90 g, 1.90 mmol) in 15 mL DMF. The clear solution was cooled to −10° C. To this, was added m-CPBA (1.48 g, 6.00 mmol) at −10° C. The reaction was allowed to warm up to room temperature, and then stirred for additional 30 min at RT. To the mixture was added TEA (0.83 mL, 6.00 mmol) and 1-methylpiperidin-4-amine (685 mg, 6.00 mmol), and then it was stirred at room temperature for 1 hour with monitoring the reaction by LC-MS. The solvent was removed under reduced pressure yielding light brown oily residue. The residue was dissolved in methylene chloride and washed with saturated aqueous sodium bicarbonate solution. The separated organic layer was dried over sodium sulfate, and then concentrated under reduced pressure to yield a solid. The solid was dissolved in a minimum amount of methylene chloride and treated with excess of n-hexanes yielding pale yellow solids. The resulted solids were collected by filtration, rinsed with n-hexanes and then dried in the air yielding a pale yellow solid. The solid was dissolved in the mixture of DCM and methanol. To the clear solution was added 4N HCl in dioxane (12.0 mL), then it was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure yielding the desired product (238, 90% yield).

Provenance & Evidence