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-Eintrag

ord-a95c49d72ce0490fafa98d752a9964c4

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08853230B2