N,1-dimethyl-1H-indole-3-carboxamide → 1-Methyl-3-(methylaminomethyl)indole

HRID 1297355

反応式

HRID 1297355 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][NH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[CH:12]=1)=O>C1COCC1>[CH3:20][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([CH2:9][NH:8][CH3:7])=[CH:12]1

参加物

4

反応物 2

HCID 5152277N,1-dimethyl-1H-indole-3-carboxamideHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 109867781-Methyl-3-(methylaminomethyl)indole収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of LiAlH4 in THF (1.0 M, 5.20 mL, 5.2 mmole) was slowly added via syringe to a solution of N,1-dimethyl-1H-indole-3-carboxamide (0.50 g, 2.6 mmole) in anhydrous THF (15 mL). Gas was evolved during the addition of the first 2 mL of LiAlH4 solution. When the addition was complete, the resulting light yellow solution was heated at gentle reflux. After 23 hr, the reaction was cooled in ice and quenched by the sequential dropwise addition of H2O (0.5 mL), 1.0 N NaOH (0.5 mL), and H2O (0.5 mL). The mixture was stirred for 15 min, then was filtered through celite®, and the filter pad was washed thoroughly with THF. The filtrate was concentrated and the residue was flash chromatographed on silica gel (10% MeOH/CHCl3 containing 0.5% conc. NH4OH) to afford the title compound (0.30 g, 67%) as a light yellow oil: MS (ES) m/e 175 (M+H)+.

後処理

  1. additionWhen the addition
  2. temperaturethe resulting light yellow solution was heated at gentle reflux
  3. temperaturethe reaction was cooled in ice
  4. customquenched by the sequential dropwise addition of H2O (0.5 mL), 1.0 N NaOH (0.5 mL), and H2O (0.5 mL)
  5. filtrationwas filtered through celite®
  6. washthe filter pad was washed thoroughly with THF
  7. concentrationThe filtrate was concentrated
  8. customchromatographed on silica gel (10% MeOH/CHCl3 containing 0.5% conc. NH4OH)

出典と根拠

ORDレコード
ord-0db36637864c4295a83aea49d9ac2426
出典データセット
uspto-grants-2007_07
特許番号
US07250424B2

関連ノート

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