Propylamine → HCID 67834777, compound

Participants

Reaction Steps

A mixture of E-indole-6-acrylic acid (0.96 g), 4-dimethylaminopyridine (0.635 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.96 g) was dissolved in methylene chloride (50 ml) and N,N-dimethylformamide (60 ml) and stirred for 1 hour. Propylamine (0.591 g) was added and stirring continued for 18 hr. Further quantities of 4-dimethylaminopyridine (0.635 g), the carbodiimide (0.96 g) and propylamine (0.591 g) were added; and the mixture stirred for a further 30 hr. The solvents were evaporated; the residue partitioned between ethyl acetate and 1M hydrochloric acid; and the organic phase washed with water and brine; dried (MgSO4); and evaporated. The residue was purified by flash chromatography, eluting with 1:10 methanol:chloroform, to give E-N-propylindole-6-acrylamide (0.7 g, 60%) as an off-white solid; partial NMR (250 MHz, DMSO-d6): 0.89(t, 3H, CH2CH2CH3, 1.48(m, 2H, CH2CH2CH3), 3.15(m, 2H, CH2CH2CH3); 6.44(d, J=2.8 Hz H3 -indole), 6.55(d, J=15.7 Hz, 1H, olefinic H), 8.00(br t, 1H, NHCO), 11.28(br s, 1H, H1 -indole).

Provenance & Evidence