Synthesis and structure of N-substituted (1-ferrocenylethyl)amine derivatives

• DOI: 10.1007/s11224-006-9118-x
• Publication Date: 2007-01-23T19:44:08Z
• Authors: Mojca Čakić Semenčić; Maja Dropučić; Lidija Barišić; Krešimir Molčanov; Vladimir Rapić
• Keywords: Carboxylate; Tertiary amine

N-Acetyl-(1-ferrocenylethyl)amine (8) was synthesized by N-acylation of (1-ferrocenylethyl)amine (7) in 84% yield. Reaction of N-acetyl-[1-(1'-bromo-ferrocenyl)ethyl]amine (4) (which was prepared by multistep sequence starting from bromoferrocene) with n-BuLi/ ClCOOEt gave 77% of N-acetyl-N-ethoxycarbonyl-(1-ferrocenylethyl)amine (6) instead of the expected ethyl 1'-[1-(acetamido)ethyl]ferrocene-1-carboxylate (5). Both structures were undoubtedly confirmed by (HR)MS, spectroscopy and single crystal X-ray structure analysis.