Water → HCID 20313224, compound

Participants

Reaction Steps

To a mixture of 2.77 g. of 3-isopropylamino-1-(3-methyl-1-oxo-5-indanyloxy)-2-propanol, 50 ml. of methylene chloride, and 1.2 g. of triethylamine was added dropwise 2.1 g. of bromoacetyl bromide with stirring under ice-cooling and the mixture was stirred for 18 hours at room temperature. Thereafter, methylene chloride was distilled off and after adding to the residue formed 50 ml. of benzene and 50 ml. of water to form a solution, the benzene layer formed was recovered, washed with 20 ml. of aqueous 5% hydrochloric acid solution and then twice each with 30 ml. of water, dried over anhydrous magnesium sulfate. Then, benzene was distilled off from the reaction mixture and after adding to the residue a solution of 0.3 g. of metallic sodium in 50 ml. of methanol, the mixture was refluxed for 3 hours. Methanol was distilled off and then to the residue were added 50 ml. of benzene and 30 ml. of water. The benzene layer formed was recovered from the mixture, washed twice with 20 ml. of aqueous 5% hydrochloric acid solution and then 20 ml. of water, and dried over anhydrous magnesium sulfate. Then, benzene was distilled off and 2 ml. of acetone was added to the residue to form precipitates, which were recovered by filtration. Thus, 2.3 g. (yield 73.6%) of 4-isopropyl-2-(3-methyl-1-oxo-5-indanyloxymethyl)-5-oxomorpholine was obtained. By recrystallizing the product from acetone, the faint yellow crystals of the product melting 150°-152° C. were obtained.

Provenance & Evidence