ANTINEOPLASTIC AGENTS: X. N-BIS(2-FLUOROETHYL)AMINES

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Abstract
Successive conversion of N-bis(2-hydroxyethyl)-p-toluenesulphonamide (Ib) to respective dimethanesulphonate and difluoro derivatives (IIa, IIIa, and IIIc) was found to provide a convenient route to N-bis(2-fluoroethyl)amine. Reaction of N-bis(2-methanesulphonyl-oxyethyl)-p-toluenesulphonamide (IIIa) with limited quantities of potassium fluoride, in several pro tic solvents, was shown to yield N-(p-toluenesulphonyl)morpholine (IV). Utility of N-bis(2-fluoroethyl)amine as a precursor of fluoro-nitrogen mustards was illustrated by synthesis of two N-bis(2-fluoroethyl)benzylamines (IXb and Xa). Application of an aluminum chloride – lithium aluminum hydride reagent for hydrogenolysis of carbon–fluorine bonds was also suggested.