Ammonium Chloride → 3-Ethyl-6-benzyloxy-7-methoxy-2-(3,4,5-trimethoxybenzyl)tetrahydroisoquinoline

Participants

Reaction Steps

A solution of 261 (297 mg, 1.0 mmol) in anhydrous DMF (3.0 mL), DIPEA (264 mg, 2.0 mmol) and 3,4,5-trimethoxybenzyl chloride (238 mg, 1.1 mmol) was heated to 80° C. for 12 h, cooled to room temperature and poured into water (50 mL) and ammonium chloride (saturated, 2 mL). The mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography using Flashmaster (SiO2: 20 g, hexane 100% to hexane/ethyl acetate 50:50). The title compound was obtained as pale yellow oil (350 mg, 73%). 1H NMR (270 MHz, CDCl3) δ 0.97 (3H, t, J 7.0, CH2CH3), 1.43 (1H, sept, J 7.0, one of CH2CH3), 1.67 (1H, sept, J 7.0, one of CH2CH3), 2.42-2.58 (1H, m, one of ArCH2CH), 2.72-2.95 (2H, m, one of ArCH2CH, CHN), 3.51-3.74 (4H, m, 2×ArCH2N), 3.80 (3H, s, OCH3), 3.83 (6H, s, 2×OCH3), 3.88 (3H, s, OCH3), 5.10 (2H, s, OCH2Ph), 6.45-6.56 (1H, m, CH), 6.56-6.70 (3H, m, 3×CH), 7.24-7.52 (5H, m, OCH2C6H5).

Provenance & Evidence