Hydrochloric Acid → HCID 20393357, compound

Participants

Reaction Steps

A suspension of 15.0 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid methylamide in 190 ml. of dimethylformamide is treated under an atmosphere of argon with 8.25 g. of potassium tertiary butylate and the mixture is stirred in an ice-bath for 15 minutes. At 0°-5° C., there is then added a solution of 0.1 mol. of diethylaminoethyl chloride in 150 ml. of toluene (freshly prepared from the corresponding hydrochloride and dried over sodium sulfate), the mixture is stirred first at room temperature for 30 minutes and then at 100° C. for 30 minutes. After cooling, the toluene is removed by distillation under reduced pressure and the residual solution poured on to 600 ml. of ice-water. The separated thick oil is extracted with methylene chloride, and the extract washed with a saturated sodium chloride solution, dried over sodium sulfate and concentrated to dryness. The residue obtained is dissolved in 60 ml. of isopropanol and treated with 9.0 g. of N-cyclohexylsulfamic acid. 200 Ml. of diethyl ether are gradually added and the mixture is left to stand at room temperature for 1 hour. The almost colorless salt which crystallizes out is removed by filtration, washed with a small amount of diethyl ether and dried in a desiccator. Recrystallization from acetone yields 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [2-(diethylamino)ethyl]methylamide cyclohexanesulfamate having a melting point of 166°-168° C. (decomposition).

Provenance & Evidence