Benzonitrile → 1-Phenyl-cyclopropylamine

To benzonitrile (1.03 g, 10 mmol) in ether (50 ml) at −70° C. was added Ti(OiPr)4 (3.22 ml, 11 mmol) and EtMgBr (3M in ether, 7.34 mL, 22 mmol) dropwise, the resulting yellow suspension was warmed up to room temperature over 1 h. After stirring for additional 30 min, the dark brown solution was added BF3.Et2O (2.47 mL, 20 mL) at room temperature. The mixture was further stirred for 1 h, and was quenched by 1N HCl (30 mL) and 5N NaOH (30 mL), the suspension was extracted with ether, ether layer was combined, concentrated to give crude residue, which was purified by column (Hexanes/EtOAc, 2:1 to 1:9) to give 1-phenylcyclopropanamine (420 mg).

1. stirringThe mixture was further stirred for 1 h
2. customwas quenched by 1N HCl (30 mL) and 5N NaOH (30 mL)
3. extractionthe suspension was extracted with ether, ether layer
4. concentrationconcentrated
5. customto give crude residue, which
6. customwas purified by column (Hexanes/EtOAc, 2:1 to 1:9)

ORD record

ord-823b6ae9ef4b4d1da721d56cc0e4d230

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367689B2