Dimethylformamide → 3-(3-(Dimethylamino)propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

HRID 24510

반응식

HRID 24510 반응식
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[CH3:11][N:12]([CH3:25])[CH2:13][CH2:14][CH2:15][C:16]1[C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[NH:18][CH:17]=1.[OH-].[Na+]>O.ClCCl>[CH3:25][N:12]([CH3:11])[CH2:13][CH2:14][CH2:15][C:16]1[C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[NH:18][C:17]=1[CH:3]=[O:4]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 111484413-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indole

생성물 1

HCID 112300633-(3-(Dimethylamino)propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Dimethylformamide (0.8 g) and 13 mL of dichloromethane was cooled to −9° C. Phosphorus oxychloride (1.7 g) was. rapidly added via a dropping funnel. 3-(3-dimethylamino-propyl)-4,5,6,7-tetrahydro-1H-indole (2 g) was added in portions with vigorous stirring. The mixture was warmed to room temperature and then refluxed for 10 minutes. It was then cooled to 5° C., and diluted with 20 mL of water. The pH was adjusted to 10 with 10N sodium hydroxide. The layers were separated. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated to give 1.8 g (80%) of 3-(3-dimethylaminopropyl)-2-formyl-4,5,6,7-tetrahydro-1H-indole as a dark oil which solidified.

후처리

  1. additionrapidly added via a dropping funnel
  2. temperaturerefluxed for 10 minutes
  3. temperatureIt was then cooled to 5° C.
  4. customThe layers were separated
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

출처 및 근거

ORD 기록
ord-1a1bb55b85f84b11ab22d5d0a05b92a7
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855730B2

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