反応 #7544

反応方程式

sodium hydroxide

1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinylcarbamate

hydrochloric acid

water

→

1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinamine

溶媒

ethyl acetate

ethyl acetate

反応条件

後処理

1. 1
   workup.ADDITIONwas added to the solution
2. 2
   温度after which the resulting mixture was heated
3. 3
   温度under reflux for 1 hour
4. 4
   温度After the reaction mixture was cooled
5. 5
   その他the organic layer was separated
6. 6
   洗浄The organic layer was washed with water
7. 7
   乾燥a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONdistilled under reduced pressure
9. 9
   その他to remove the solvent
10. 10
    その他The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 20:1)

実験手順

In 7.0 mL of ethyl acetate was dissolved 1.12 g of tert-butyl=1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinylcarbamate, and 1.86 mL of 6 mol/L hydrochloric acid was added to the solution, after which the resulting mixture was heated under reflux for 1 hour. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 10 with a 2 mol/L aqueous sodium hydroxide solution, and the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 20:1) to obtain 0.38 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-pyrrolidinamine as a light-yellow oil.

出典