Benzoyl chloride → HCID 23093472, compound

To a mixture of 2-(methylamino)ethanol (30.04 g) and ethyl acetate (90 mL) was added a mixture of di-tert-butyl dicarbonate (87.30 g) and ethyl acetate (10 mL) under ice-cooling. The reaction solution was stirred at room temperature for 1 hr, and benzoyl chloride (61.8 g) and pyridine (38.8 mL) were added thereeto under ice-cooling. The reaction solution was stirred at room temperature for 1 hr, and solid was filtered off. The solid was washed with ethyl acetate (100 mL), and the filtrate and washings were combined and washed with water (100 mL), then saturated saline (100 mL). The solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL), and added 4N hydrogen chloride-ethyl acetate solution (200 mL), followed by stirring at room temperature for 30 minutes. Diethyl ether (100 mL) was added thereto, and solid was collected by filtration. After washing two times with ethyl acetate (100 mL), the solid was dried at 60° C. under reduced pressure to give title compound as white solid (57.4 g).

1. additionwas added
2. temperaturecooling
3. temperatureunder ice-cooling
4. stirringThe reaction solution was stirred at room temperature for 1 hr
5. filtrationsolid was filtered off
6. washThe solid was washed with ethyl acetate (100 mL)
7. washwashed with water (100 mL)
8. dry with materialThe solution was dried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
11. additionadded 4N hydrogen chloride-ethyl acetate solution (200 mL)
12. stirringby stirring at room temperature for 30 minutes
13. additionDiethyl ether (100 mL) was added
14. filtrationsolid was collected by filtration
15. washAfter washing two times with ethyl acetate (100 mL)
16. customthe solid was dried at 60° C. under reduced pressure

ORD record

ord-ee0f9e4719044a7a8b741cc8912468a6

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2