Hydrochloric Acid → HCID 53892805, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N,N-dimethyl-3-(2-allyl-4-butoxyphenoxy)propylamine (1.8 g) in tetrahydrofuran (3 ml) was added dropwise over a period of 3 minutes to a solution of borane tetrahydrofuran complex (1M, 12.4 ml) at a temperature of 0° C. and under an atmosphere of argon. The reaction mixture was stirred at 0° C. for 3 hours. Ethanol (10 ml) was added to the reaction mixture, followed by aqueous 6N aqueous sodium hydroxide and hydrogen peroxide solution (30%, 12 ml). The mixture was then heated at 50° C. for 1.5 hours. The reaction mixture was cooled to ambient temperature, extracted with ethyl acetate, the ethyl acetate extracts dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel (Merck Art No 9385) using a 40:60:0.2 mixture of ethyl acetate, hexane and triethylamine as eluent to give an oil. The oil was dissolved in ether and excess ethereal hydrogen chloride added until crystallisation began. The solid was collected by filtration and dried to give N,N-dimethyl-3-[4-butoxy-2-(3-hydroxypropyl)phenoxy]propylamine as a white solid (60 mg), m.p. 118° C.; microanalysis, found: C, 62.4; H, 9.6; N, 4.0% C18H32NO3Cl requires: C, 62.5; H, 9.32; N, 4.05%; NMR ([CD3 ]2SO+CD3COOD): 0.95(3H,t), 1.45(2H,m), 1.7(4H,m), 2.2(2H,m), 2.58(2H,t), 2.89(6H,s), 3.35(2H,t), 3.55(2H,t), 3.9(2H,t), 4.02(2H,t), 6.72(2H,m) and 6.82(1H,s); m/z 310(M+H).

Provenance & Evidence