Amantadine → (3S)-N-1-Adamantyl-1-phenylpiperidine-3-carboxamide

Participants

Reaction Steps

4-Methylmorpholine (43 μL, 0.00039 mol) was added to a mixture of (3S)-1-phenylpiperidine-3-carboxylic acid (20 mg, 0.0001 mol), tricyclo[3.3.1.13,7]decane-1-amine (18 mg, 0.00012 mol), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (53.2 mg, 0.000102 mol) or benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (45.2 mg, 0.000102 mol) in N,N-dimethylformamide (0.5 mL, 0.006 mol). The reaction mixture was stirred at rt for 2 hrs and the crude reaction mixture was purified by prep-LCMS to afford the desired product. LCMS: m/z 339.3 (M+H)+.

Provenance & Evidence