Wang Chao-jie
2006
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Fine chemicals
Abstract
N~1-(4-Phthalimide)butyl-N~1,N~4-ditert-butoxycarbonylbutane-1,4-diamine(Ⅳ) was prepared by the tandem reactions of substitution and protection using N-tert-butoxycarbonylbutane-1,4-diamine and N-(4-bromobutyl)phthalimide as the starting materials.Then Ⅳ was treated with hydrazine hydrate to remove its phthalimide group to give N~1-(4-aminobutyl)-N~1,N~4-di-tert-butoxycarbonylbutane-1,4-diamine(Ⅴ).Total yield of these three steps is 38%.Ⅴ was condensed with 9-anthraldehyde,then the crude product was reduced with NaBH_4.After purification,the reduced product was deprotected to provide N~1-(4-aminobutyl)-N~4-(9-anthracenylmethyl)butane-1,4-diamine trihydrochloride salt(Ⅶ) with 75% total yield in these three steps.Structures of Ⅳ~Ⅶ were confirmed by ~(13)CNMR,~1HNMR and ESI-MS.The reaction conditions were also prelimiarily optimized.