Sodium Iodide → 1-(4-{2-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinolin-6-yl}phenyl)ethanone

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Reaction Conditions

Reaction Steps

To a stirred solution of 1-[4-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-phenyl]-ethanone (216 mg, 0.86 mmol) in acetonitrile (5.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (186 mg, 0.86 mmol, 1.0 eq.), K2CO3 (238 mg, 1.72 mmol, 2.0 eq.) and NaI (50 mg). The resulting mixture is stirred at 50° C. overnight. Water (10.0 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3). The combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.01 (2H, d), 7.66 (2H, d), 7.36˜7.44 (2H, m), 7.12 (1H, d), 3.74 (2H, s), 3.60˜3.70 (4H, m), 3.38 (2H, s), 2.97 (2H, t), 2.83 (2H, t), 2.66 (1H, m), 2.64 (3H, s), 2.29 (4H, m), 1.60˜2.08 (6H); MS (+VE) m/z 432.2 (M++1).

Provenance & Evidence