Hydrochloric Acid → N-nonanoyl tyramine

Participants

Reaction Steps

Procedure--Nonanoyl chloride (2.74 m, 14.6 mmol) was added dropwise to a cooled solution of tyramine (1 g, 7.29 mmol) and triethylamine (2.03 ml, 14.6 mmol) in THF (35 ml). The reaction mixture was stirred at room temperature for 48 hours. It was then poured into 10% HCl solution (70 ml) and the mixture was then extracted with ethyl acetate (3×50 ml). The ethyl acetate layer was separated, dried (MgSO4) and concentrated under reduced pressure to give crude N-nonanoyl tyramine. The product was purified by chromatography on a silica gel column eluted with methylene chloride/ethyl acetate (30:1). m.p. 65.9° to 66.7° C. IR (KBr) 3306, 2922, 2851, 1638; 1H NMR δ 6.65-6.98 (d of d, 4 H, aromatic), 7.78 (t, 1 H, NH), 9.15 (s, 1 H, OH). Analysis calculated for C17H27NO2 : C, 73.61; H, 9.81; N, 5.05. Found C, 73.49; H, 9.661; N, 5.31.

Provenance & Evidence