Water → HCID 57017083, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (51 mg) was added portionwise over a period of 5 minutes to a stirred solution of N,N-dimethyl-3-[4-butoxy-2-(3-hydroxypropyl)phenoxy]propylamine (330 mg) in tetrahydrofuran (8 ml) at a temperature of 0° C. and under an atmosphere of argon. The reaction mixture was allowed to warm to 25° C. and stirred for a further 0.5 hour. The reaction mixture was cooled to 0° C. and methyl iodide (0.4 ml) added. The reaction mixture was allowed to warm to 25° C. and the reaction mixture was stirred for a further 15 hours. The reaction mixture was poured into water (15 ml) and extracted with ethyl acetate (4×15 ml). The ethyl acetate extracts were combined, washed with water (10 ml), dried (MgSO4) and evaporated to give a yellow oil. The oil was purified by flash column chromatography on silica gel (Merck Art No 9385) using a 75:25:0.2 mixture of ethyl acetate, hexane, and triethylamine as eluent to give N,N-dimethyl-3-[4-butoxy-2-(3-methoxypropyl)phenoxy]propylamine as a yellow oil (70 mg), NMR ([CD3 ]2SO): 0.92(3H,t), 1.42(2H,m), 1.70(4H,m), 2.1(2H,m), 2.5(6H,s), 2.9(2H,m) and 3.2(3H,s), 3.31(2H,t), 3.9(4H,m), 6.7(2H,s), and 6.82(1H,d); m/z 324 (M+H). The N,N-dimethyl-3-[4-butoxy-2-(3-hydroxypropyl)phenoxy]propylamine used as starting material was prepared as follows.

Provenance & Evidence