Hydrochloric Acid → 1-Ethyl-1-(2-methanesulfonyl-thiazol-5-yl)-propylamine hydrochloride

Participants

Reaction Steps

To a chilled (0° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (100 mg, 0.3 mmol) in THF (5 mL) is added a 2 M solution of ethylmagnesium chloride (0.19 mL, 0.38 mmol) in diethyl ether. After 2.5 hours, the reaction mixture is quenched with saturated aqueous ammonium chloride (10 mL) and extracted with EtOAc (2×10 mL). The combined organic layers are washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane to afford an oil. The oil is dissolved in methanol (5 mL) and a 4 N solution of HCl in dioxane (0.5 mL, 2 mmol) is added. After 1 hour, the solution is concentrated to obtain the title compound.

Provenance & Evidence