Propylamine → HCID 19069300, compound

Participants

Reaction Steps

To a stirred solution of 1.06 g (5.0 mmol, 1 eq.) of 4-phenylaminobenzoic acid (Portnaya, B. S., Turitsyna, N. F., Bobkova, T. P., and Levkeov, I. I., Zhur. Obshchei. Khim., 30, 2693 (1960)), n-propylamine (0.82 mL, 10.0 mmol, 2 eq.), and 0.061 g (0.5 mmol, 0.1 eq.) of DMAP in THF at 0° C. was added 1.05 g (5.5 mmol, 1.1 eq.) of EDCl. The mixture was stirred overnight while the bath melted. The mixture was poured into 150 mL of ethyl acetate and washed with 50 mL each of water, 1N aqueous HCl, water and saturated aqueous NaHCO3. The ethyl acetate layer was then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (80 g SiO2, 1:1 ethyl acetate-hexanes) to give 0.51 g (40%) of the title compound. 1H NMR (300 MHz, CDCl3) δ10.57 (bs, 2H), 7.21-7.41 (m, 9H), 3.96 (s, 2H), 2.75 (m, 2H), 1.64 (hextet, 2H), 0.92 (t, 3H). MS (DCl) m/e 255 (M+H)+.

Provenance & Evidence