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

1964 ◽  
Vol 42 (3) ◽  
pp. 572-578 ◽  
Author(s):  
George R. Pettit ◽  
Robert L. Smith
Keyword(s):  
Aluminum Chloride ◽  
Antineoplastic Agents ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Potassium Fluoride ◽  
Lithium Aluminum ◽  
Nitrogen Mustards ◽  
Convenient Route

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.

ANTINEOPLASTIC AGENTS: XI. N-BIS(2-BROMOETHYL)AMINES

1964 ◽  
Vol 42 (7) ◽  
pp. 1699-1706 ◽  
Author(s):  
George R. Pettit ◽  
Maurice R. Chamberland ◽  
David S. Blonda ◽  
Martyn A. Vickers
Keyword(s):  
Exchange Reaction ◽  
Antineoplastic Agents ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Efficient Synthesis ◽  
Nitrogen Mustards ◽  
Hydride Reduction ◽  
Halogen Exchange ◽  
Convenient Route

A novel halogen exchange reaction was found to accompany condensation of an acyl chloride with N-bis(2-bromoethyl)amine. Reaction between an acyl bromide and N-bis(2-bromoethyl)amine, however, gave the expected N-bis(2-bromoethyl)amide. A number of N-alkyl-N-bis(2-bromoethyl)amines were prepared by lithium aluminum hydride reduction of the corresponding N-bis(2-bromoethyl)amides. The overall transformation from N-bis(2-bromoethyl)amine presents a convenient route to certain bromo nitrogen mustards. An efficient synthesis of N-bis(2-iodoethyl)amine hydroiodide is also described.

ANTINEOPLASTIC AGENTS: IX. N-BENZYL-N-BIS(2-HALOETHYL)AMINES

1963 ◽  
Vol 41 (12) ◽  
pp. 2962-2968 ◽  
Author(s):  
George R. Pettit ◽  
David S. Blonda ◽  
Ernest C. Harrington
Keyword(s):  
Cancer Chemotherapy ◽  
Aluminum Chloride ◽  
Antineoplastic Agents ◽  
Sodium Iodide ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Nitrogen Mustards ◽  
Convenient Procedure ◽  
Hydride Reduction

A number of N-bis(2-chloroethyl)amines and three N-bis(2-iodoethyl)benzylamines have been prepared for cancer chemotherapy studies. The chloro-nitrogen mustards were readily obtained by aluminum chloride – lithium aluminum hydride reduction of the corresponding N-bis(2-chloroethyl)amides. A convenient procedure for converting N-bis(2-chloroethyl)-benzylamine hydrochlorides to N-bis(2-iodoethyl)benzylamine hydroiodides, employing sodium iodide, was also developed.

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