Diisopropylethylamine → HCID 59553352, compound

Participants

Reaction Steps

4-(2-Chloroethoxy)-naphthalen-1-ylamine hydrochloride salt (482 mg, 1.86 mmol), 3-fluoro-5-piperidinylbenzoic acid (500 mg, 2.2 mmol), diisopropylethylamine (1.14 ml, 6.7 mmol) and HBTU (1.06 g, 2.8 mmol) are stirred at room temperature in anhydrous dimethylformamide (10 ml) for 1 day. The mixture is poured into ethyl acetate (200 ml) and washed with water (3×100 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by column chromatography on silica gel eluted with 20% ethyl acetate in hexanes to give N-[4-(2-chloroethoxy)-naphthalen-1-yl]-3-fluoro-5-piperidin-1-yl-benzamide as a tan solid (650 mg).

Provenance & Evidence