Triethylamine → Trans-(+/-)-N-[2-(1-pyrrolidinyl)cyclohexyl]-N,2,3-trimethyl-1H-indole-5-acetamide

関与物質

反応手順

Triethylamine (139 μl, 1 mmol) was added to a solution of 2,3-dimethyl-1H-indole-5-acetic acid (203 mg, 1 mmol) in tetrahydrofuran (10 ml) at -15° C., with vigorous stirring. Ethyl chloroformate (96 μl, 1 mmol) was added, and the mixture stirred for five minutes. A solution of trans-(±)-N-methyl-2-(1-pyrrolidinyl)cyclohexanamine (182 mg, 1 mmol) in tetrahydrofuran (2 ml) was added, and stirring continued for 30 minutes at -15° C., then 30 minutes at room temperature. The reaction was evaporated to small volume, the residue taken into ethyl acetate (50 ml), and washed with saturated sodium bicarbonate solution (3×50 ml). The organic extract was dried (MgSO4), evaporated under reduced pressure and recrystallized from ethyl acetate to yield the amide (204 mg, 56%); VmaxC=0 1615 cm-1.

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