Triethylamine → 5-Propylpyrimidin-2-ylpiperidin-4-yl methanesulfonate

Participants

Reaction Steps

To a mixture of 1-(5-propylpyrimidin-2-yl)piperidin-4-ol (16.1 g, 72.8 mmol) and triethylamine (10.14 mL, 72.8 mmol) in CH2Cl2 (150 mL) at 0° C. was added methanesulfonyl chloride (4.76 mL, 80 mmol) slowly. After stirring at rt for 1.5 h, the mixture was quenched with 15 ml water followed by 15 ml 1N HCl. The organic layer was collected and the aqueous layer was extracted with CH2Cl2. The combined organic layers were then washed with saturated aqueous NaHCO3 and brine. After drying over Na2SO4, the organic layer was concentrated to give the desired product 1-(5-propylpyrimidin-2-yl)piperidin-4-yl methanesulfonate (21 g, 70.1 mmol, 96% yield) as yellow solid. MS (ESI) 300.2 (M+1).

Provenance & Evidence