Sodium Iodide → 1-(4-cyclobutyl-piperazin-1-yl)-2-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone

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Reaction Steps

To a stirred solution of 6-methoxy-1,2,3,4-tetrahydroisoquinoline (163 mg, 1.0 mmol) in acetonitrile (5.0 ml) is added 2-chloro-(4-cyclobutyl-piperazine)-acetamide (216 mg, 1.0 mmol, 1.0 eq.), K2CO3 (376 mg, 2.0 mmol, 2.0 eq.), and NaI (30 mg). The resulting mixture is stirred at rt overnight. Water (10.0 ml) is added to quench the reaction, and then the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3). The extracts are dried over sodium sulfate, and the solvent is removed under reduced pressure to yield a residue that is purified through PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 6.92 (1H, d), 6.70 (1H, dd), 6.63 (1H, d), 3.77 (3H, s), 3.58˜3.68 (6H, m), 3.33 (2H, s), 2.86 (2H, t), 2.74 (2H, t), 2.65 (1H, m), 2.27 (4H, m), 1.62˜2.06 (6H, m); MS (+VE) m/z 344.2 (M++1).

Provenance & Evidence