The synthesis of primary, secondary, and tertiary ferrocenylethylamines

Abstract

A simplified procedure for the preparation of α-N,N-dialkylaminoethylferrocenes R2NR′ (R = Me, C6H11, CHMe2; R′ = CH(CH3)C5H4FeC5H5) from the alcohol R′OH by treatment with HBr and R2NH is described. Use of ammonia results in the isolation of R′NH2, R′2NH (major product) and R′3N and use of the optically active amine d-(+)-H2NCH(CH3)C6H5 gives rise to diastereomers R′NHCH(CH3)C6H5 which are separable. When diphenylphosphine is substituted for an amine the oxide R′P(O)Ph2 is obtained in low yield. The secondary amine R′2NH reacts with n-butyllithium and chlorodiphenylphosphine to afford R′2NPPh2.