Dimethylbarbituric acid → 4-Amino-1-benzylpiperidin-2-one

Participants

Reaction Steps

A mixture of racemic 4-allylamino-1-benzyl-piperidin-2-one (430 mg, 1.76 mmol), 1,3-dimethyl barbituric acid (824 mg 5.28 mmol) and Pd(PPh3)4 (204 mg, 0.18 mmol) in DCM (20 mL) was stirred at ambient temperature for 2 hours then concentrated under vacuum. The resulting residue was purified by Isolute® SCX-2 column (gradient: DCM to 5 to 60% 2M NH3 in methanol solution in DCM) to afford 260 mg (72%) of racemic 4-amino-1-benzyl-piperidin-2-one. LCMS (Method H, ESI): RT=0.35 min, m+H=204.9; 1H NMR (400 MHz, CDCl3) δ: 7.29 (m, 5H), 4.60 (m, 2H), 3.34-3.13 (m, 3H), 2.74 (ddd, 1H), 2.37-2.23 (m, 1H), 2.01 (m, 3H), 1.64 (m, 1H).

Provenance & Evidence