Sodium Azide → Ethyl 4-(4-azidopiperidin-1-yl)benzoate

To a solution of ethyl 4-(4-(methylsulfonyloxy)piperidin-1-yl)benzoate (10.5 g, 32.1 mmol) in DMF (50 mL) was added sodium azide (4.17 g, 64.2 mmol). The mixture was heated at 80° C. for 5 hours, cooled to room temperature, diluted with brine (300 mL), and extracted with ethyl acetate (400 mL). The organic phase was washed with brine (2×300 mL), dried over anhydrous MgSO4, filtered, and concentrated, to afford ethyl 4-(4-azidopiperidin-1-yl)benzoate as a yellow solid (7.62 g, 87%).

1. temperaturecooled to room temperature
2. extractionextracted with ethyl acetate (400 mL)
3. washThe organic phase was washed with brine (2×300 mL)
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-812e8beb9d2a47bfa20ec2b47e93414f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2