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Synthesis of [2H7]indatraline.

Synthesis of [2H7]indatraline.

Journal of labelled compounds & radiopharmaceuticals (2014-11-11)

L Allmendinger, K T Wanner

ABSTRACT

Deuterium-labelled indatraline was synthesized in high efficiency employing a Friedel-Crafts alkylation of [(2)H6]benzene with (E)-3-(3,4-dichlorophenyl)acrylic acid as a key step. The desired labelling of the final compound was ascertained in two ways, by incorporation of [(2)H6]benzene in the target molecule and additionally by deuterium transfer to the non-deuterated aryl moiety of the Friedel-Crafts alkylation product from [(2)H6]benzene, the latter thus serving as reagent and solvent.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Aluminum chloride, anhydrous, sublimed, ≥98%

Sigma-Aldrich

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

Sigma-Aldrich

Rhein

Sigma-Aldrich

N,N-Dimethylformamide, Molecular Biology, ≥99%

Supelco

Dimethylformamide, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Aluminum chloride, anhydrous, powder, 99.999% trace metals basis

Sigma-Aldrich

Aluminum chloride, ReagentPlus^®, 99%

Sigma-Aldrich

Aluminum chloride, powder, 99.99% trace metals basis

Sigma-Aldrich

Aluminum chloride, reagent grade, 98%

Sigma-Aldrich

Aluminum chloride, 99.99% trace metals basis

Sigma-Aldrich

Aluminum chloride solution, 1.0 M in nitrobenzene

Supelco

N,N-Dimethylformamide, analytical standard

Sigma-Aldrich

N,N-Dimethylformamide, ReagentPlus^®, ≥99%

Sigma-Aldrich

N,N-Dimethylformamide, suitable for HPLC, ≥99.9%

Sigma-Aldrich

N,N-Dimethylformamide, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.8% (GC)

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

Sigma-Aldrich

N,N-Dimethylformamide, biotech. grade, ≥99.9%

Sigma-Aldrich

N,N-Dimethylformamide, ACS reagent, ≥99.8%

Sigma-Aldrich

Rhein, technical grade

Sigma-Aldrich

Methylamine solution, 40 wt. % in H₂O

Sigma-Aldrich

Methylamine solution, 2.0 M in methanol

Sigma-Aldrich

Benzene, suitable for HPLC, ≥99.9%

Supelco

Benzene, analytical standard

Sigma-Aldrich

Benzene, ACS reagent, ≥99.0%

Sigma-Aldrich

Benzene, anhydrous, 99.8%

Supelco

Benzene, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Benzene, puriss. p.a., reag. Ph. Eur., ≥99.7%