Water → 4-(Aminomethyl)benzonitrile

Triphenylphosphine (7.67 g) is added to a solution of 4-(azidomethyl)-benzonitrile (4.19 g) in THF (30 mL) and stirred for 1 hr. Water (10 mL) is added, and the solution is stirred for 16 hrs. The reaction mixture is diluted with ether (50 mL) and extracted with HCl (3 N, 3×25 mL) and water (1×25 mL). The aqueous phases are combined and washed with ether (50 mL). Sodium hydroxide is added until the pH =12. After extracting with ether (2×50 mL), the solution is dried with MgSO4 and filtered. The solvent is evaporated under reduced pressure. The resulting crude mixture is then purified via bulb to bulb distillation at 150° C. and 1 torr to afford 1.74 g (50%) of the title compound as a clear, colorless oil.

1. stirringthe solution is stirred for 16 hrs
2. extractionextracted with HCl (3 N, 3×25 mL) and water (1×25 mL)
3. washwashed with ether (50 mL)
4. additionSodium hydroxide is added until the pH =12
5. extractionAfter extracting with ether (2×50 mL)
6. dry with materialthe solution is dried with MgSO4
7. filtrationfiltered
8. customThe solvent is evaporated under reduced pressure
9. distillationThe resulting crude mixture is then purified via bulb to bulb distillation at 150° C.

ORD record

ord-340c8efdf9b44840aee1df1754f7709c

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06093732