反応 #1459596

反応方程式

dimethylformamide

3-(3-morpholin-4-yl-propyl)-4,5,6,7-tetrahydro-1H-indole

sodium hydroxide

phosphorus oxychloride

→

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

収率 83.0%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   温度The mixture was refluxed at 60° C. for 4 hours
2. 2
   温度cooled in an ice bath
3. 3
   workup.ADDITIONIce cubes were slowly added to the mixture
4. 4
   workup.STIRRINGThe mixture was stirred at room temperature for 30 minutes
5. 5
   抽出extracted with ethyl acetate
6. 6
   洗浄The organic layer was washed with brine
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   濃縮concentrated
9. 9
   その他to give crude product which
10. 10
    その他was purified on a silica gel column
11. 11
    洗浄eluting with dichloromethane-methanol-ammonium hydroxide (98:2:1)

実験手順

To an ice-cooled solution of 0.32 mL (4.1 mmol) of dimethylformamide in 3 mL of dichloromethane was added dropwise 0.4 mL (4.1 mmol) of phosphorus oxychloride. The reaction mixture was stirred at room temperature for 15 minutes and a solution of 680 mg (2.7 mmol) of 3-(3-morpholin-4-yl-propyl)-4,5,6,7-tetrahydro-1H-indole in 20 mL of dichloromethane was added dropwise at 0° C. The mixture was refluxed at 60° C. for 4 hours and cooled in an ice bath. Ice cubes were slowly added to the mixture followed by addition of 2 N sodium hydroxide to pH 12. The mixture was stirred at room temperature for 30 minutes and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give crude product which was purified on a silica gel column eluting with dichloromethane-methanol-ammonium hydroxide (98:2:1) to give 600 mg (83% yield) of 3-(3-morpholin-4-yl-propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde as a dark red oil. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 11.33 (s, br, 1H, NH). MS m/z 277 [M+1].

出典