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

HRID 24510

反応式

HRID 24510 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1a1bb55b85f84b11ab22d5d0a05b92a7
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

関連ノート

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