3-Amino-1-propanol → HCID 54039693, compound

Participants

Reaction Steps

A mixture of 4.5 g of 3-(3-pyridyl)acrylic acid, 3.5 g of N-hydroxysuccinimide, 6.8 g of dicyclohexylcarbodiimide, and 80 ml of dioxane is stirred at room temperature overnight. The reaction mixture is filtered, and the filtrate is concentrated to give a brown oil. The product is dissolved in 100 ml of tetrahydrofuran, and 2.3 g of 3-amino-1-propanol is added. The mixture is stirred at room temperature overnight and concentrated. The residue is chromatographed on silica gel with chloroform-methanol (30:1) to give 4.2 g of N-[3-(3-pyridyl)acryloyl]-3-amino-1-propanol. The product is converted into the hydrochloride with 35 w/v % ethanolic hydrogen chloride. To the hydrochloride is added 4.6 g of thionyl chloride, and the mixture is stirred at 100° C. for 2 hours. The remaining thionyl chloride is distilled off, and 50 ml of water is added. The resulting solution is neutralized with 10% aqueous sodium carbonate solution and extracted with three 50-ml portions of chloroform. The combined extracts are dried over magnesium sulfate, and the chlorofom is distilled off. The residue is chromatographed on silica gel with chloroform-methanol (30:1) to give 3.2 g of N-[3-(3-pyridyl)acryloyl]-3-amino-1-chloropropane.

Provenance & Evidence