A Convenient Synthesis of Unsymmetrical N,N′-Disubstitutedα,ω-Diaminoalkanes

Liliana R. Orelli Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956 (1113), Buenos Aires, Argentina Fax: E-mail: E-Mail: [email protected]

Alejandra Salerno Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956 (1113), Buenos Aires, Argentina Fax: E-mail: E-Mail: [email protected]

Mónica E. Hedrera Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956 (1113), Buenos Aires, Argentina Fax: E-mail: E-Mail: [email protected]

Isabel A. Perillo Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956 (1113), Buenos Aires, Argentina Fax: E-mail: E-Mail: [email protected]

Abstract

A general procedure is described for regiospecific construction of unsymmetrical N-alkyl (or aralkyl)-N′-aryl-α,ω-diaminoalkanes 3 (n=2,3,4) by reduction of N-(ω -arylaminoalkyl)amides 2 with borane. Compounds 2 are readily obtained by condensation of N-(ω-haloalkyl)amides 1 with aromatic amines.

Notes

Reaction between N-(4-chlorobutyl)benzamide and aliphatic amines leads preferentially to N-benzoylpyrrolidine (unpublished results)

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A Convenient Synthesis of Unsymmetrical N,N′-Disubstitutedα,ω-Diaminoalkanes

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A Convenient Synthesis of Unsymmetrical N,N′-Disubstitutedα,ω-Diaminoalkanes

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