3-Methoxyphenethylamine → HCID 60063665, compound

Participants

Reaction Steps

(3-Methoxyphenyl)ethylamine 14 (5.73 gm, 0.038 moles), ethyl 4-bromobutyrate (9.60 gm, 0.049 moles) and diisopropylethylamine (6.40 gm, 0.050 moles) were heated at 110-120° C. overnight, cooled, and partitioned between 100 ml DCM and 100 ml water. The aqueous layer was extracted twice with 50 ml portions of DCM. The combined organic extracts were washed with saturated NaCl, dried over Na2SO4, filtered, and concentrated by rotary evaporation under reduced pressure. The crude product was purified by flash chromatography on silica gel, eluting with a gradient mixture of ethyl acetate and hexane. Ethyl 4-[ethyl(3-methoxyphenyl)amino]butanoate 15 (9.6 gm, 95% yield) was isolated as a slightly yellow oil after removing the solvent. 1H NMR (CDCl3) δ 7.12, 1H, t; 6.31, 1H, d; 6.22, 2H, m; 4.12, 2H, q; 3.79, 3H, s; 3.3, 4H, m; 2.35, 2H, t; 1.9, 2H, m; 1.26, 3H, t; 1.14, 3H, t.

Provenance & Evidence