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Amination of Aryl Halides and Esters Using Intensified Continuous Flow Processing.

Amination of Aryl Halides and Esters Using Intensified Continuous Flow Processing.

Molecules (Basel, Switzerland) (2015-10-02)

Thomas M Kohl, Christian H Hornung, John Tsanaktsidis

ABSTRACT

Significant process intensification of the amination reactions of aryl halides and esters has been demonstrated using continuous flow processing. Using this technology traditionally difficult amination reactions have been performed safely at elevated temperatures. These reactions were successfully conducted on laboratory scale coil reactor modules with 1 mm internal diameter (ID) and on a preparatory scale tubular reactor with 6 mm ID containing static mixers.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Ammonia-¹⁴N, 99.99 atom % ¹⁴N

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Methylamine solution, 33 wt. % in absolute ethanol ((denatured with 1% toluene))

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Ammonia solution, 0.4 M in THF

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Ammonia solution, 2.0 M in isopropanol

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Methylamine solution, 2.0 M in THF

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Methylamine solution, 2.0 M in methanol

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Methanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)

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Methanol, puriss., meets analytical specification of Ph Eur, ≥99.7% (GC)

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Methanol, ACS reagent, ≥99.8%

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Isopropyl alcohol, ≥99.7%, FCC, FG

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Ammonia solution, 0.4 M in dioxane

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Methanol, Absolute - Acetone free

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Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

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Ammonia solution, 4 M in methanol

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Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer

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4-Bromopyridine hydrochloride, 99%

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Methylamine, ≥99.0%

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer