Sodium Bicarbonate → 4-(2-Aminoethyl)benzonitrile

Participants

Reaction Steps

Dissolve 4-(2-amino-ethyl)-benzonitrile hydrochloride (300 mg, 1.65 mmol) into saturated aqueous NaHCO3 and extract twice with EtOAc. Dry the combined organic extracts over Na2SO4 and concentrate in vacuo to obtain 4-(2-amino-ethyl)-benzonitrile (205 mg, 85%). Dissolve 4-(2-amino-ethyl)-benzonitrile (200 mg, 1.37 mmol) in DCM (2 mL), add triethylamine (54 μL, 0.38 mmol) and cool the mixture at 0° C. Add 2,2-dimethyl-propionyl chloride (169 μL, 1.37 mmol) dropwise and allow to stir the mixture at 0° C. for 15 min and at room temperature for 2 h. Add water, separate the organic phase and extract the aqueous phase twice with DCM. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (182 mg, 58%).

Provenance & Evidence