Benzenemethanamine, 4-bromo-N-(cyclopropylmethyl)-N-methyl- synthesis

Yield:1089130-99-3 78%

Reaction Conditions:

with potassium carbonate;potassium iodide in toluene;acetonitrile at 40;Sealed tube;

Steps:

General Procedure A: alkylation with potassium carbonate

General procedure: Amine (0.25 mmol), and bromide (0.25 mmol) were taken up in acetonitrile (0.3 mL) in a conical vial equipped with a stirrer bar. Potassium carbonate (0.5 mmol) was added followed by potassium iodide (10 mol%) if required. The vial was sealed with a screwcap and the reaction was stirred at 40 °C until thin layer chromatography (TLC) indicated complete consumption of the starting materials. A precipitate was formed during the reaction which was removed by filtration and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography and sent to the Netherlands Cancer Institute (NKI) for biological testing.

References:

Milne, Kirsty;Sun, Jianhui;Zaal, Esther A.;Mowat, Jenna;Celie, Patrick H.N.;Fish, Alexander;Berkers, Celia R.;Forlani, Giuseppe;Loayza-Puch, Fabricio;Jamieson, Craig;Agami, Reuven [Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,# 18,p. 2626 - 2631] Location in patent:supporting information