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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Preparation of 1° Amines: Azide Synthesis01:22

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Síntesis verde de las morfolinas a través de la monoalquilación selectiva de aminas

Kacey G Ortiz1, Andrew T Brusoe1, Jason An1

  • 1Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877-0368, United States.

Journal of the American Chemical Society
|October 17, 2024
PubMed
Resumen
Este resumen es generado por máquina.

Un nuevo y eficiente método sintetiza morfolinas a partir de alcoholes 1,2-amino utilizando sulfato de etileno. Este protocolo simple y de alto rendimiento ofrece beneficios ambientales y de seguridad sobre los enfoques tradicionales para crear estos compuestos farmacéuticos y agrícolas vitales.

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Área de la Ciencia:

  • Química orgánica
  • Química medicinal
  • Química sintética

Sus antecedentes:

  • Las morfolinas son andamios heterocíclicos cruciales en los productos farmacéuticos y agroquímicos.
  • Las rutas sintéticas existentes de los alcoholes 1,2-amino a las morfolinas a menudo son ineficientes y complejas.

Objetivo del estudio:

  • Desarrollar un protocolo simple, de alto rendimiento y neutro en oxígeno para la síntesis de morfolina.
  • Establecer un método de monoalquilación selectiva para los alcoholes 1,2-amino utilizando sulfato de etileno.

Principales métodos:

  • Un protocolo de uno o dos pasos que utiliza reactivos de bajo costo: sulfato de etileno y terciobutoxido de potasio (tBuOK).
  • Exploración de las condiciones de reacción para lograr un aislamiento limpio de los productos de monoalquilación a través de la reacción SN2.
  • Investigación de la selectividad dependiente de la estructura y el papel de las propiedades del sulfato de etileno.

Principales resultados:

  • Síntesis exitosa de varias morfolinas con sustituyentes en diferentes posiciones.
  • Escalabilidad demostrada con ejemplos preparados en una escala de > 50 g.
  • Se informó de la síntesis formal de una morfolina de una amina primaria.
  • Mostró la utilidad del sulfato de etileno en la síntesis de piperazinas y como electrofilo de 2 carbonos.

Conclusiones:

  • El método desarrollado proporciona una alternativa eficiente, respetuosa con el medio ambiente y más segura para la síntesis de morfolina.
  • La fácil monoalquilación selectiva de aminas primarias es una ventaja clave de esta nueva metodología.
  • El sulfato de etileno presenta un reactivo versátil para la síntesis de heterociclos que contienen nitrógeno y en reacciones de acoplamiento de fragmentos.