反応 #352172

反応方程式

3-Dipropylamino-5-methyloxycarbonylchroman

Sodium hydroxide

diphenylphosphoryl azid

→

title compound

3-Dipropylamino-5-aminochroman

溶媒

Methanol

methanol

water

反応条件

後処理

1. 1
   温度the solution was refluxed with nitrogen overnight
2. 2
   その他The solution was evaporated to dryness, toluene (20 ml)
3. 3
   workup.ADDITIONwas added
4. 4
   その他again the solution was evaporated to dryness
5. 5
   workup.DISSOLUTIONThe residue was dissolved in toluene 20 ml
6. 6
   温度the solution was refluxed for 2 hours
7. 7
   温度reflux
8. 8
   温度The solution was cooled
9. 9
   洗浄washed with water
10. 10
    抽出extracted with dilute HCl (aq.)
11. 11
    抽出extracted with toluene
12. 12
    乾燥The toluene-phase was dried with sodium sulphate
13. 13
    その他evaporated to dryness
14. 14
    workup.DISSOLUTIONThe residue was dissolved in ethanol containing 10% NaOH (20 ml)
15. 15
    温度the solution was refluxed overnight
16. 16
    温度The solution was cooled
17. 17
    workup.ADDITIONdiluted with toluene
18. 18
    洗浄Washing with water
19. 19
    その他drying of the organic phase and evaporation to dryness

実験手順

3-Dipropylamino-5-methyloxycarbonylchroman (Example 2; 1.0 g, 3.4 mmol) was dissolved in methanol (20 ml). Sodium hydroxide (0.16 g, 4.1 mmol) in water (1.0 ml) was added and the solution was refluxed with nitrogen overnight. The solution was evaporated to dryness, toluene (20 ml) was added and again the solution was evaporated to dryness. The residue was dissolved in toluene 20 ml, diphenylphosphoryl azid (1.87 g, 6.8 mmol) was added and the solution was refluxed for 2 hours. Methanol (2.0 ml) was added and reflux was continued for 4 hours. The solution was cooled, washed with water and extracted with dilute HCl (aq.). The acidic water phase was neutralized NaOH (aq.) and extracted with toluene. The toluene-phase was dried with sodium sulphate and evaporated to dryness. The residue was dissolved in ethanol containing 10% NaOH (20 ml) and the solution was refluxed overnight. The solution was cooled and diluted with toluene. Washing with water, drying of the organic phase and evaporation to dryness afforded the title compound as an oil, which was converted to a dihydrochloride salt. Mp 173°-174° C.

出典