Pyridine → 2-(2H-Benzotriazol-2-yl)ethan-1-amine

Temperature

-50 °C

4.70 g Of the 2-(2-benzotriazolyl)ethanol (28.8 mmol) was dissolved in 200 ml diethyl ether and 2.28 g pyridine (28.8 mmol) was added. The mixture was cooled to -50° C., and 8.18 g triflic anhydride (29 mmol) was added. The mixture was removed from the cooling bath, and was allowed to reach room temperature. The mixture was filtered under dry conditions and added to a cold -40° C. solution of ca 150 ml ammonia in 50 ml diethyl ether. This mixture was allowed to reach room temperature, and ether was removed. 50 ml 2M HCl was added, and this mixture was washed with methylene chloride. The aqueous phase was made basic by addition of 50 ml 25% sodium hydroxide and extracted with 3×25 ml methylene chloride. Evaporation of the solvent gave 2.10 g 2-(2-benzotriazolyl)ethylamine (12.9 mol). This amine was used in the next step without further purification.

1. customThe mixture was removed from the cooling bath
2. customto reach room temperature
3. filtrationThe mixture was filtered under dry conditions
4. additionadded to a cold -40° C. solution of ca 150 ml ammonia in 50 ml diethyl ether
5. customto reach room temperature
6. customether was removed
7. addition50 ml 2M HCl was added
8. washthis mixture was washed with methylene chloride
9. additionThe aqueous phase was made basic by addition of 50 ml 25% sodium hydroxide
10. extractionextracted with 3×25 ml methylene chloride
11. customEvaporation of the solvent

ORD record

ord-f222e08f99fd4d0bb3045e84e14a97e1

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05714503