Phenethylamine → HCID 66598115, compound

Participants

Reaction Steps

To a stirred yellow solution of VII (362.5 mg, 1.062 mmol) in anhydrous THF (10 mL) was added phenethylamine (142 mg, 147 μL, 1.1×1.062 mmol) and then, dropwise, triethylamine (118 mg, 164 μL, 1.1×1.062 mmol). The solution was stirred for 1 hour at room temperature. The colorless solution was then diluted with CH2Cl2 and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (1:1, v/v) to yield 203 mg (56%) of 12 as a clear light yellow oil: Rf=0.45 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 7.28 (td, 3J=7.4 Hz, 2H), 7.20 (tt, 3J=7.4 Hz, 1H), 7.16 (d, 3J=7.3 Hz, 2H), 6.98 (d, 3J=8.0 Hz, 1H), 6.93 (d, 1H), 6.90 (dd, 3J=8.0 Hz, 1H), 5.04 (s, 2H, CH2O), 4.73 (bs, 1H, NH), 3.81 (s, 3H, OCH3), 3.45 (q, 3J=6.6 Hz, 2H, NCH2), 2.80 (t, 3J=6.9 Hz, 2H, PhCH2) and 2.29 (s, 3H). Exact mass (ESI) calculated for C19H22NO5 [M+H]=344.1492. found 344.1496.

Provenance & Evidence