Hydrochloric Acid → HCID 53899394, compound

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Reaction Steps

A solution of N-isopropyl-3-(2-allyl-4-butoxy-phenoxy)propylamine (404 mg) in ethanol (15 ml) was hydrogenated at ambient temperature and pressure for 8 hours using a catalyst of palladium on carbon (10% w/w, 80 mg). The catalyst was removed by filtration and the filtrate evaporated to give a yellow oil. The oil was purified by flash column chromatography on silica gel (Merck Art No 9385) using a 70:30:1 mixture of ethyl acetate, hexane and triethylamine to give an oil. The oil was dissolved in ether and excess ethereal hydrogen chloride was added until crystallisation began. The solid was collected by filtration and recrystallised from ethyl acetate to give N-isopropyl-3-(4-butoxy-2-propylphenoxy)propylamine (271 mg) as a white solid, m.p. 102 103° C.; microanalysis, found: C, 65.7; H, 10.2; N, 4.0%; C19H34NO2Cl. 0.25H2O requires: C, 65.5; H, 9.98; N, 4.02%; NMR ([CD3 ]2SO): 0.90(6H,m), 1.28(6H,d), 1.52(6H,m), 2.12(2H,m), 2.5(2H,m), 3.04(2H,m), 3.3(1H,m), 3.88(2H,t), 4.0(2H,t), 6.7(2H,t) and 6.85(1H,d); m/z 308 (M+H).

Provenance & Evidence