(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrile → (+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzylamine

Participants

Reaction Steps

Bubble nitrogen into a solution of (±)-4-[1-(2,2-dimethylpropyl-carbamoyl)-ethyl]-benzonitrile (80 mg, 0.33 mmol) in methanol (9 mL) with 2 drops of concentrated HCl for 10 min. Add 10% Pd/C (Degussa type E101, 8 mg) and submit the mixture to hydrogenation at atmospheric pressure overnight. Filter the catalyst over Celite® and concentrate the filtrate in vacuo. Partition the solid between saturated aqueous NaHCO3 and EtOAc, and extract again with EtOAc. Dry the combined organics extracts over MgSO4, filter and concentrate in vacuo to afford the title compound as a yellow oil (69 mg, 85%). MS (ES+) m/z: 249 (M+H)+.

Provenance & Evidence