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

41639

Sigma-Aldrich

Dimethyl sulfoxide, BioUltra, Molecular Biology, ≥99.5% (GC)

74875

Sigma-Aldrich

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

B80429

Sigma-Aldrich

4-Bromopyridine hydrochloride, 99%

D2438

Sigma-Aldrich

Dimethyl sulfoxide, sterile-filtered, BioPerformance Certified, meets EP, USP testing specifications, suitable for hybridoma

108987

Sigma-Aldrich

Methyl 3-mercaptopropionate, 98%

D4540

Sigma-Aldrich

Dimethyl sulfoxide, ≥99.5% (GC), suitable for plant cell culture

D8418

Sigma-Aldrich

Dimethyl sulfoxide, Molecular Biology

I9516

Sigma-Aldrich

2-Propanol, BioReagent, ≥99.5%, Molecular Biology

D9170

Sigma-Aldrich

Dimethyl sulfoxide, PCR Reagent

D1435

Sigma-Aldrich

Dimethyl sulfoxide, meets EP testing specifications, meets USP testing specifications

733458

Sigma-Aldrich

2-Propanol, electronic grade, 99.999% trace metals basis

190764

Sigma-Aldrich

2-Propanol, ACS reagent, ≥99.5%

109827

Sigma-Aldrich

2-Propanol, Laboratory Reagent, ≥99.5%

I9030

Sigma-Aldrich

Isopropyl alcohol, meets USP testing specifications

59304

Sigma-Aldrich

2-Propanol, BioUltra, Molecular Biology, ≥99.5% (GC)

59300

Sigma-Aldrich

2-Propanol, puriss. p.a., ACS reagent, ≥99.8% (GC)

D2650

Sigma-Aldrich

Dimethyl sulfoxide, Hybri-Max^™, sterile-filtered, BioReagent, suitable for hybridoma, ≥99.7%

676853

Sigma-Aldrich

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

D65100

Sigma-Aldrich

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

472301

Sigma-Aldrich

Dimethyl sulfoxide, ACS reagent, ≥99.9%

494453

Sigma-Aldrich

Dichloromethane, biotech. grade, 99.9%, contains 40-150 ppm amylene as stabilizer

320269

Sigma-Aldrich

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

D5879

Sigma-Aldrich

Dimethyl sulfoxide, ReagentPlus^®, ≥99.5%

534102

Sigma-Aldrich

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

717975

Sigma-Aldrich

Methanol, suitable for NMR (reference standard)

718939

Sigma-Aldrich

Ammonia solution, 0.4 M in THF

426466

Sigma-Aldrich

Methylamine solution, 40 wt. % in H₂O

395056

Sigma-Aldrich

Methylamine solution, 2.0 M in THF

395048

Sigma-Aldrich

Methylamine solution, 2.0 M in methanol

608777

Sigma-Aldrich

Ammonia-¹⁴N, 99.99 atom % ¹⁴N