N,N-Dimethylethylenediamine → HCID 67300491, compound

Participants

Reaction Steps

A 250 mg portion of 2-ethyl-1-(4-fluorobenzyl)-3-methyl-1H-indole-5-carboxylic acid, 231 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 54 mg of 1-hydroxybenzotriazole were dissolved in 8 ml of N,N-dimethylformamide, and then 106 mg of N,N-dimethyl-1,2-ethanediamine was added, followed by overnight stirring at room temperature. The reaction liquid was diluted with chloroform and then washed with a 1 M sodium hydroxide aqueous solution and saturated brine, and dried over anhydrous sodium sulfate. After evaporation of the solvent under a reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=100:1:0.1 to 50:1:0.1 to 30:1:0.1) to obtain 257 mg of N-[2-(dimethylamino)ethyl]-2-ethyl-1-(4-fluorobenzyl)-3-methyl-1H-indole-5-carboxamide as a colorless oily material. This product was dissolved in 2.5 ml of acetonitrile at 80° C., and 67 mg of oxalic acid was added, followed by stirring at 80° C. for 10 minutes and then stirring at room temperature for 2 hours. The resulting solid was collected by filtration and then washed with acetonitrile to obtain 236 mg of N-[2-(dimethylamino)ethyl]-2-ethyl-1-(4-fluorobenzyl)-3-methyl-1H-indole-5-carboxamide oxalate as a pale purple solid.

Provenance & Evidence