N-LITHIO-N-(2-LITHIOETHYL)- AND N-LITHIO-N-(3-LITHIOPROPYL)-BENZAMIDE: DIRECT PREPARATION AND SYNTHETIC APPLICATIONS OF 2-LITHIOETHYL- AND 3-LITHIOPROPYL-AMINE EQUIVALENTS

Article abstract of DOI:10.1016/S0040-4020(01)80078-8

The successive reaction of 2-chloroethyl and 3-chloropropyl-benzamide with n-butyl-lithium and lithium naphthalenide at temperatures ranging between -78 and -50 deg C leads to N-lithio-N-(2-lithioethyl)- and N-lithio-N-(3-lithiopropyl)benzamide <(8), (9)>, which by treatment with different electrophiles (H2O, D2O, Me2S2, CO2, PrⁱCHO, PhCHO, Me2CO, Ph2CO, and O2) yields the expected functionalized benzamides <(10), (11)>.The acidic and basic hydrolysis of compounds (10) and (11) gives different results depending on the structure of the substrate and the reaction conditions.