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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, anhydrous, ≥99.98%

Sigma-Aldrich

Methanol, anhydrous, 99.8%

Sigma-Aldrich

Methylamine solution, 2.0 M in THF

Sigma-Aldrich

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

Sigma-Aldrich

Ammonia-¹⁴N, 99.99 atom % ¹⁴N

Sigma-Aldrich

Ammonia solution, 0.4 M in THF

Sigma-Aldrich

Ammonia solution, 4 M in methanol

Sigma-Aldrich

Methylamine solution, 2.0 M in methanol

Sigma-Aldrich

Methylamine solution, 40 wt. % in H₂O

Sigma-Aldrich

Methanol, BioReagent, ≥99.93%

Sigma-Aldrich

Methanol, NMR reference standard

Sigma-Aldrich

Isopropyl alcohol, ≥99.7%, FCC, FG

Sigma-Aldrich

Methanol, Absolute - Acetone free

Sigma-Aldrich

Methanol, ACS spectrophotometric grade, ≥99.9%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Ammonia solution, 0.4 M in dioxane

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Methanol, Laboratory Reagent, ≥99.6%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Ammonia solution, 2.0 M in isopropanol

Sigma-Aldrich

Ammonia solution, 2.0 M in ethanol

Sigma-Aldrich

Ammonia solution, 7 N in methanol

Sigma-Aldrich

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

Sigma-Aldrich

8-Octanoyloxypyrene-1,3,6-trisulfonic acid trisodium salt, suitable for fluorescence, ≥90% (HPCE)

Sigma-Aldrich

4-Bromopyridine hydrochloride, 99%

Sigma-Aldrich

Methyl 3-mercaptopropionate, 98%

Sigma-Aldrich

2-Propanol, anhydrous, 99.5%

Sigma-Aldrich

Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer

Sigma-Aldrich

2-Propanol, BioUltra, for molecular biology, ≥99.5% (GC)

Sigma-Aldrich

Dimethyl sulfoxide, BioUltra, for molecular biology, ≥99.5% (GC)