Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

A solution of NaH (0.026 g, 0.60 mmol, 55% in mineral oil) is added into a solution of 3-chloro-9H-carbazole (0.100 g, 0.50 mmol) in anhydrous THF (5 mL). After 30 min of stirring at rt a solution of (±)-3-nitro-benzenesulfonic acid oxiranylmethyl ester in anhydrous THF (0.5 mL) is added. After 90 min of stirring at rt a solution of 1-cyclohexyl piperazine (0.25 g, 1.50 mmol) in anhydrous THF (1 mL) is then added. The resulting mixture is allowed to stir at 60° C. for 15 hours. The reaction mixture is quenched with brine (15 mL) and extracted with Et2O (50 mL+2×25 mL). After drying over MgSO4, evaporation under reduced pressure, the crude compound is purified via flash chromatography on a 3×24 cm2 SiO2 column using EtOAc/MeOH (8/1) and (4/1) as eluant. A solution of the purified above compound (0.088 g, 0.21 mmol, 41%) is treated with HCl (1M in Et2O) to give the title compound hydrochloride (0.085 g, 0.17 mmol) as a white powder in a 34% yield.

Provenance & Evidence