Réaction #79273

Équation de réaction

1-bromo-3-chloropropane

indoline

Et3N

→

1-(3-Chloro-1-propyl)indoline

Rendement 45.4%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to 20° C.
2. 2
   Autrequenched by addition of H2O
3. 3
   ExtractionThe product was extracted with Et2O
4. 4
   LavageThe organic solution was then washed with H2O and brine
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of 1-bromo-3-chloropropane (1.98 g, 12.6 mmol) and indoline (500 mg, 4.20 mmol) in 1,4-dioxane (6.0 mL) was added Et3N (2.12 g, 21.0 mmol) at 20° C. The reaction mixture was then stirred for 15 h at 70° C. The reaction mixture was cooled to 20° C. and quenched by addition of H2O. The product was extracted with Et2O. The organic solution was then washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. 1-(3-Chloro-1-propyl)indoline (373 mg, 45%) was isolated by flash chromatography on a silica gel column by elution with EtOAc/Hexanes a pale yellow oil. 1H NMR (CDCl3, 300 MHz) δ2.07 (qu, 2H, J=6.2 Hz), 2.97 (t, 2H, J=8.2 Hz), 3.24 (t, 2H, J=6.6 Hz), 3.35 (t, 2H, J=8.3 Hz), 3.68 (t, 2H, J=6.2 Hz), 6.50-6.56 (m, 1H), 6.66 (t, 1H, J=6.6 Hz), 7.04-7.10 (m, 2H) ppm.

Source