4-Toluenesulfonyl chloride → HCID 54315052, compound

Participants

Reaction Steps

To a mixture of (1-methylpiperidin-2-yl)methanol (1.00 g, 7.75 mmol) in dry DMF (5.0 mL) at 0° C. was added NaH (620 mg, 15.5 mmol, 60% in mineral oil). After being stirred for 1 h, TsCl (2.96 g, 15.5 mmol) in DMF (1.0 mL) was added. The resulting mixture was further stirred at room temperature for 10 h and then poured into the ice-water (20 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The organic layers were dried over Na2SO4 and evaporated to dryness to afford the crude product, which was purified by silica gel chromatography eluting with a 20% gradient of EtOAc in petroleum ether to afford (1-methylpiperidin-2-yl)methyl 4-methylbenzenesulfonate (800 mg, 36.5% yield). LCMS (ESI) m/z: 284.2 [M+H+]

Provenance & Evidence