Sodium Carbonate → HCID 22596144, compound

Participants

Reaction Steps

To a stirred solution of 1-(3′,4′-dimethoxyphenyl)pentylamine (0.3 grams, 1.34 mmol) and sodium carbonate (0.15 grams, 1.45 mmol) in a mixture of water (10 milliliters) and acetonitrile (10 milliliters) was added N-carbethoxyphthalimide (0.29 grams, 1.34 mmol). The resulting solution was stirred for 3 hours at room temperature, the acetonitrile was evaporated and a two phase mixture resulted. The organic phase was extracted into methylene chloride, dried over magnesium sulfate and concentrated to afford 0.41 grams of crude product as an oil. The crude product was purified by flash chromatography (silica gel, 30% ethyl acetate/hexane) to afford 0.18 grams (38%) of the product as an oil: 1H NMR (CDCl3) δ7.88-7.63(m, 4H), 7.20-7.07(m, 2H),6.82-6.76(m, 1H), 5.34-5.18(m, 1H), 3.89(s, 3H), 3.85(s, 3H),2.66-2.43(m, 1H),2.40-2.17(m, 1H), 1.50-1.20(m, 2H), 0.96-0.81(m, 3H). 13C NMR (CDCl3) δ1.68.5, 148.8, 148.5, 133.8, 132.5, 131.9, 123.1, 120.6, 111.6, 110.8, 55.9, 55.8, 55.0, 30.9, 29.2, 22.3, 13.9.

Provenance & Evidence