Synthesis and molecular structures of (2-dialkylaminophenyl)alcohols and of 2-phenylaminoalkyl-dimethylaminobenzene derivatives

N,N-Dimethyl-o-toluidine, N,N-dimethylaniline, and N,N-diethylaniline were treated with n-butyllithium-tmeda in diethyl ether-hexane solution to give o-lithioarylamines, which react with various electrophiles (benzophenone, dicyclohexyl ketone, benzaldehyde, and Ph(H)C=NPh) to form the corresponding (2-dialkylaminophenyl)alcohols 1-HOCPh2-2-NMe2C6H4 (1), 1-HOCCy2-2-NMe2C6H4 (2), 1-HOCPh2CH2-2-NMe2C6H4 (4), l-HOC(H)PhCH2-2-NMe2C6H4 (6), and 1-HOCPh2-2-NEt2C6H4 (7), and the 2-phenylaminoalkyl-dimethylaminobenzene derivatives 1-NMe2-2-NH(Ph)C(H)PhC6H4 (3) and 1-NMe2-2-NH(Ph)C(H)PhCH2C6H4 (5). Compounds 1-7 were characterized spectroscopically (NMR, IR, MS) and by crystal structure determination. (C) 2003 Elsevier Ltd. All rights reserved.