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ChemicalBook CAS DataBase List 2-(2-METHYL-1H-INDOL-1-YL)ETHANAMINE

2-(2-METHYL-1H-INDOL-1-YL)ETHANAMINE synthesis

3synthesis methods
-

Yield:883535-89-5 99%

Reaction Conditions:

with tetra(n-butyl)ammonium hydrogensulfate;sodium hydroxide in toluene; for 17 h;Reflux;Inert atmosphere;

Steps:

A.1.1.1 A.1.1.1. 2-(2-Methyl-1 H-indol-1-yl)ethan-1-amine

To a solution of 2-methylindole (10.04 g, 75 mmol) in toluene (200 mL) are added 2-chloroethylamine hydrochloride (17.4 g, 150 mmol), freshly powdered NaOH (21.00 g, 525 mmol) and tetrabutyl ammonium hydrogen sulfate (2.037 g, 6 mmol). The resulting mixture is heated up to reflux and stirred for 17h. It is then cooled down to RT, and filtered through a filter paper. The residue is triturated twice with toluene, and filtrated. The filtrate is concentrated under reduced pressure, and the residue is purified by FC, using a gradient of DCM/MeOH from 100:0 to 95:5. After concentration of the product containing fractions, the title compound (13.2 g, 99%) is obtained as a yellow resin: LC-MS A: tR = 0.54 min; [M+H]+ = 175.31.

References:

WO2017/85198,2017,A1 Location in patent:Page/Page column 120