An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines

Autores
Mollo, María Cruz; Gruber, Nadia; Díaz, Jimena Estela; Bisceglia, Juan Angel; Orelli, Liliana Raquel
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
N-Alkylation is conceptually the most straightforward disconnection towards secondary and tertiary amines. Although this transformation seems rather simple, the factthat the newly formed amines are also nucleophilic brings about the formation of bisand/or polyalkylation by-products. Thus, the crude reaction mixture often contains the desired product together with the starting amine and variable amounts of collateral products, all of them with similar Rf values, a fact that complicates the chromatographic purification of the desired compounds. In this context, new methodologies combining operational simplicity, high yields, readily available starting materials and low cost reagents are desirable for the high throughput preparation of the target compounds. Thiswork describes a practical method for the synthesis of tertiary N-alkyl-N-aryltetra- and pentamethylenediamines 3, by selective monoalkylation of N-alkylanilines with ω−haloalkylnitriles followed by reduction. The optimized reaction conditions resulted in an efficient procedure, of remarkable selectivity in the alkylation step and high overall yields of the diamines.
Fil: Mollo, María Cruz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Bisceglia, Juan Angel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Materia
Putrescine
Cadaverine
N-Alkylation
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/30340
Acceder
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network_name_str CONICET Digital (CONICET)
spelling An efficient synthesis of N-alkyl-N-arylputrescines and cadaverinesMollo, María CruzGruber, NadiaDíaz, Jimena EstelaBisceglia, Juan AngelOrelli, Liliana RaquelPutrescineCadaverineN-Alkylationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1N-Alkylation is conceptually the most straightforward disconnection towards secondary and tertiary amines. Although this transformation seems rather simple, the factthat the newly formed amines are also nucleophilic brings about the formation of bisand/or polyalkylation by-products. Thus, the crude reaction mixture often contains the desired product together with the starting amine and variable amounts of collateral products, all of them with similar Rf values, a fact that complicates the chromatographic purification of the desired compounds. In this context, new methodologies combining operational simplicity, high yields, readily available starting materials and low cost reagents are desirable for the high throughput preparation of the target compounds. Thiswork describes a practical method for the synthesis of tertiary N-alkyl-N-aryltetra- and pentamethylenediamines 3, by selective monoalkylation of N-alkylanilines with ω−haloalkylnitriles followed by reduction. The optimized reaction conditions resulted in an efficient procedure, of remarkable selectivity in the alkylation step and high overall yields of the diamines.Fil: Mollo, María Cruz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Bisceglia, Juan Angel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaTaylor & Francis2014-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/30340Mollo, María Cruz; Gruber, Nadia; Díaz, Jimena Estela; Bisceglia, Juan Angel; Orelli, Liliana Raquel; An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines; Taylor & Francis; Organic Preparations and Procedures International; 46; 5; 9-2014; 444-4520030-49481945-5453CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1080/00304948.2014.944404info:eu-repo/semantics/altIdentifier/url/http://www.tandfonline.com/doi/abs/10.1080/00304948.2014.944404info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:23:04Zoai:ri.conicet.gov.ar:11336/30340instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:23:04.348CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines
title An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines
spellingShingle An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines
Mollo, María Cruz
Putrescine
Cadaverine
N-Alkylation
title_short An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines
title_full An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines
title_fullStr An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines
title_full_unstemmed An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines
title_sort An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines
dc.creator.none.fl_str_mv Mollo, María Cruz
Gruber, Nadia
Díaz, Jimena Estela
Bisceglia, Juan Angel
Orelli, Liliana Raquel
author Mollo, María Cruz
author_facet Mollo, María Cruz
Gruber, Nadia
Díaz, Jimena Estela
Bisceglia, Juan Angel
Orelli, Liliana Raquel
author_role author
author2 Gruber, Nadia
Díaz, Jimena Estela
Bisceglia, Juan Angel
Orelli, Liliana Raquel
author2_role author
author
author
author
dc.subject.none.fl_str_mv Putrescine
Cadaverine
N-Alkylation
topic Putrescine
Cadaverine
N-Alkylation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv N-Alkylation is conceptually the most straightforward disconnection towards secondary and tertiary amines. Although this transformation seems rather simple, the factthat the newly formed amines are also nucleophilic brings about the formation of bisand/or polyalkylation by-products. Thus, the crude reaction mixture often contains the desired product together with the starting amine and variable amounts of collateral products, all of them with similar Rf values, a fact that complicates the chromatographic purification of the desired compounds. In this context, new methodologies combining operational simplicity, high yields, readily available starting materials and low cost reagents are desirable for the high throughput preparation of the target compounds. Thiswork describes a practical method for the synthesis of tertiary N-alkyl-N-aryltetra- and pentamethylenediamines 3, by selective monoalkylation of N-alkylanilines with ω−haloalkylnitriles followed by reduction. The optimized reaction conditions resulted in an efficient procedure, of remarkable selectivity in the alkylation step and high overall yields of the diamines.
Fil: Mollo, María Cruz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Bisceglia, Juan Angel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
description N-Alkylation is conceptually the most straightforward disconnection towards secondary and tertiary amines. Although this transformation seems rather simple, the factthat the newly formed amines are also nucleophilic brings about the formation of bisand/or polyalkylation by-products. Thus, the crude reaction mixture often contains the desired product together with the starting amine and variable amounts of collateral products, all of them with similar Rf values, a fact that complicates the chromatographic purification of the desired compounds. In this context, new methodologies combining operational simplicity, high yields, readily available starting materials and low cost reagents are desirable for the high throughput preparation of the target compounds. Thiswork describes a practical method for the synthesis of tertiary N-alkyl-N-aryltetra- and pentamethylenediamines 3, by selective monoalkylation of N-alkylanilines with ω−haloalkylnitriles followed by reduction. The optimized reaction conditions resulted in an efficient procedure, of remarkable selectivity in the alkylation step and high overall yields of the diamines.
publishDate 2014
dc.date.none.fl_str_mv 2014-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/30340
Mollo, María Cruz; Gruber, Nadia; Díaz, Jimena Estela; Bisceglia, Juan Angel; Orelli, Liliana Raquel; An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines; Taylor & Francis; Organic Preparations and Procedures International; 46; 5; 9-2014; 444-452
0030-4948
1945-5453
CONICET Digital
CONICET
url http://hdl.handle.net/11336/30340
identifier_str_mv Mollo, María Cruz; Gruber, Nadia; Díaz, Jimena Estela; Bisceglia, Juan Angel; Orelli, Liliana Raquel; An efficient synthesis of N-alkyl-N-arylputrescines and cadaverines; Taylor & Francis; Organic Preparations and Procedures International; 46; 5; 9-2014; 444-452
0030-4948
1945-5453
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1080/00304948.2014.944404
info:eu-repo/semantics/altIdentifier/url/http://www.tandfonline.com/doi/abs/10.1080/00304948.2014.944404
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Taylor & Francis
publisher.none.fl_str_mv Taylor & Francis
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.891075

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