Imidazole → HCID 68998776, compound

Temperature

2.5 °C

To a solution of (S)-1-Piperidin-2-yl-methanol hydrochloride (3.43 g, 22.63 mmol), imidazole (6.1 g, 88.72 mmol) and triethylamine (7.33 g, 72.42 mmol) in anhydrous dichloromethane (120 mL) at 0-5° C. was added a solution of thionyl chloride (3.2 g, 25.86 mmol) in anhydrous dichloromethane (10 mL) over a period of 45 min. The reaction mixture was stirred at 0-5° C. for 45 min, partitioned with H2O and the aqueous layer was extracted with dichloromethane (2×150 mL). The combined organic layer was washed with H2O dried over Na2SO4, and concentrated in vacuo to give an orange liquid. Flash column chromatography purification (silica gel, 2% EtOAc in dichloromethane) afforded the title product as a clear, colorless liquid (1.31 g, 36%).

1. custompartitioned with H2O
2. extractionthe aqueous layer was extracted with dichloromethane (2×150 mL)
3. washThe combined organic layer was washed with H2O
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customto give an orange liquid
7. customFlash column chromatography purification (silica gel, 2% EtOAc in dichloromethane)

ORD record

ord-f54947a20f254b659b97dc5b6cefaf4c

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598359B2