4-Methoxybenzylamine → 3-[(1-Amino-5-isoquinolyl)oxy]propylamine hydrochloride

Participants

Reaction Conditions

Reaction Steps

The title compound was synthesized from Intermediate 18 according to the method described in a reference (Buchwald, S. L., J. Org. Chem., 65, 1158 (2000)). That is, a suspension of Intermediate 18 (674 mg), tris (dibenzylideneacetone)dipalladium(0) (92 mg, Aldrich), 2-(di-tert-butylphosphino)biphenyl (119 mg, Strem Chemicals), 4-methoxybenzylamine (329 mg, Tokyo Kasei Kogyo) and sodium tert-butoxide (269 mg, Tokyo Kasei Kogyo) in toluene (5 ml) was stirred with heating at 80° C. under nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature and added with ethyl acetate (5 ml). The insoluble matters were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (525 mg).

Provenance & Evidence