Benzonitrile → 1-Phenyl-cyclopropylamine

To a solution of benzonitrile (1.03 g, 10 mmol) in DCM (50 mL) at −60° C. was added Ti(OiPr)4 (3.22 mL, 11 mmol) and EtMgBr (3M in ether, 7.34 mL, 22 mmol), the resulting dark brown solution was slowly warmed up to room temperature over 1 h. BF3.OEt2 (2.47 mL, 20 mmol) was added, and the solution was further stirred at room temperature for 2 h. The mixture was quenched with Sat. NH4Cl and 1N HCl, aqueous layer was separated and extracted with ether, and then neutralized with 5N NaOH to pH=10. The resulting precipitate was filtered off and the filtrate was extracted with EtOAc, EtOAc layer was combined, dried and concentrated to give 1-phenylcyclopropanamine as oil (600 mg).

1. customThe mixture was quenched with Sat. NH4Cl and 1N HCl, aqueous layer
2. customwas separated
3. extractionextracted with ether
4. filtrationThe resulting precipitate was filtered off
5. extractionthe filtrate was extracted with EtOAc, EtOAc layer
6. customdried
7. concentrationconcentrated

ORD record

ord-e6d09fb88fbb40819173fbd40769b819

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102625B2