Cesium carbonate → {1-[3-(1-Quinolin-2-yl-piperidin-4-yl)-pyrazin-2-yl]-piperidin-4-yl}-methanol

Temperature

100 °C

To a solution of [1-(3-piperidin-4-yl-pyrazin-2-yl)-piperidin-4-yl]-methanol hydrochloride (156 mg, 0.5 mmol) and 2-chloro-quinoline (81.5 mg 0.5 mmol) in DMF (5 mL) was added Cs2CO3 (325 mg, 1 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (15 mL) and brine (15 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel to give {1-[3-(1-quinolin-2-yl-piperidin-4-yl)-pyrazin-2-yl]-piperidin-4-yl}-methanol (142 mg, 0.35 mmol, yield 70.47%).

1. extractionextracted with EtOAc (2×20 mL)
2. washThe combined organic extracts were washed with water (15 mL) and brine (15 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customThe filtrate was evaporated in vacuo
6. customthe residue was purified by flash column chromatography on silica gel

ORD record

ord-cb5422ffb557424eac9cec61905dacd0

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957073B2