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-HOCCy2-2-NMe2C6H4 (), 1-HOCPh2CH2-2-NMe2C6H4 (), 1-HOC(H)PhCH2-2-NMe2C6H4 (), and 1-HOCPh2-2-NEt2C6H4 (), and the 2-phenylaminoalkyl-dimethylaminobenzene derivatives 1-NMe2-2-NH(Ph)C(H)PhC6H4 () and 1-NMe2-2-NH(Ph)C(H)PhCH2C6H4 (). Compounds were characterized spectroscopically (NMR, IR, MS) and by crystal structure determination.