反応 #63363

反応方程式

methanesulphonic acid chloride

1-(4-aminophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

water

→

title compound

1-(4-methanesulphonylaminophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

溶媒

methylene chloride

pyridine

反応条件

後処理

1. 1
   workup.WAITthe mixture is left
2. 2
   workup.WAITto stand overnight at 0°-5°
3. 3
   抽出Extraction
4. 4
   洗浄the organic phase is washed in succession with water, cold 2N hydrochloric acid, water, semi-saturated bicarbonate solution and water
5. 5
   乾燥After drying over magnesium sulphate
6. 6
   ろ過the mixture is filtered
7. 7
   濃縮concentrated by evaporation
8. 8
   その他the residue is recrystallised from methanol

実験手順

A solution of 0.31 ml of methanesulphonic acid chloride in 3 ml of methylene chloride is added at room temperature to a solution of 1.03 g of 1-(4-aminophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione and 24 mg of 4-dimethylaaminopyridine in 10 ml of pyridine. After stirring for 5 hours, 50 ml of water are added, and the mixture is left to stand overnight at 0°-5°. Extraction is carried out with methylene chloride, and the organic phase is washed in succession with water, cold 2N hydrochloric acid, water, semi-saturated bicarbonate solution and water. After drying over magnesium sulphate, the mixture is filtered and concentrated by evaporation, and the residue is recrystallised from methanol. The title compound is obtained in the form of white crystals having a melting point of 159°-160°. Rf (hexane/ethyl acetate 1:1)=0.15.

出典