反応 #52618

反応方程式

POCl3

N,N-dimethylformamide

3-[3-(4-methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole

DMF

→

3-[3-(4-methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

収率 62.0%

反応条件

後処理

1. 1
   その他to come to room temperature
2. 2
   その他to come to room temperature
3. 3
   workup.STIRRINGstirred at that temperature overnight
4. 4
   その他The reaction was then quenched with ice
5. 5
   workup.STIRRINGAfter stirring at room temperature for 1 hr
6. 6
   抽出the reaction was extracted with ethyl acetate (EtOAc)
7. 7
   その他the organic layer separated
8. 8
   洗浄washed with brine
9. 9
   その他dried
10. 10
    濃縮concentrated

実験手順

POCl3 (1.8 mL, 18.9 mmol) was added dropwise to N,N-dimethylformamide (DMF, 3.8 mL, 51.6 mmol) at −5° C. The mixture was then allowed to come to room temperature and then stirred for 30 minutes after which it was again cooled to −5° C. A solution of 3-[3-(4-methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole (4.5 g, 17.2 mmol) in DMF (9 mL) was added dropwise. The mixture was again allowed to come to room temperature and then stirred at that temperature overnight. The reaction was then quenched with ice, followed by 10 N NaOH to adjust the pH to 10-11. After stirring at room temperature for 1 hr, the reaction was extracted with ethyl acetate (EtOAc), the organic layer separated, washed with brine, dried and concentrated to give 3.1 g (62%) of 3-[3-(4-methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde.

出典