Triethylamine → N-(4-(2-tert-Butyl-4-chlorophenoxy)butyl)-4-hydroxy-3-(morpholinomethyl)-benzamide

Participants

Reaction Steps

A mixture of 4-(2-tert-butyl-4-chloro-phenoxy)-butylamine hydrochloride (0.102 g, 0.35 mmol), 4-hydroxy-3-morpholin-4-ylmethyl-benzoic acid (0.091 g, 0.385 mmol), triethylamine (54 μL, 0.385 mmol), N-hydroxybenzotriazole (0.059 g, 0.385 mmol), EDC HCl (0.074 g, 0.385 mmol) in dry DMF was stirred for 3 h at room temperature. 20 mL of a 5% sodium bicarbonate solution was added, and the reaction was extracted with dichloromethane (3×20 mL). The combined organic layers were washed with 10% hydrochloric acid (1×20 mL), brine (2×20 mL) and dried over sodium sulfate. The solvent was removed in vacuo, the residue was triturated with a mixture of diethyl ether and ethyl acetate. The crude product was purified by flash chromatography (Kieselgel 60H) using chloroform:methanol (10:3) as an eluent. Yield: 0.070 g (42%) 6-1. LCMS: method A, Rt: 1.80 min, M+H=475).

Provenance & Evidence