Hydrochloric Acid → 3-[(1S)-1-Aminoethyl]benzonitrile

Participants

Reaction Steps

(S)-1-(3-cyanophenyl)-1-azidoethane (1.42 mmol) was dissolved in benzene (4 mL), H2O (500 μL) was added followed by triphenylphosphine (2.90 mmol). The resultant mixture was heated to 80° C. for 3.5 h. 25 mL of 2N HCl was added and the mixture washed 3×20 mL diethyl ether. These washes were discarded and the aqueous phase made strongly basic by the addition of 5N NaOH. This basic aqueous phase was then extracted 3×25 mL diethyl ether, these extracts combined, washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was used without further purification (150 mg). 1H NMR (500 MHz, CDCl3): δ 7.70 (m, 1H); 7.62 (d, J=7.8 Hz, 1H); 7.54 (m, 1H); 7.44 (t, J=7.8 Hz, 1H); 4.20 (q, J=6.6 Hz, 1H); 1.40 (d, J=6.6 Hz, 3H).

Provenance & Evidence