Ethyl Acetate → 3-[2-(Dimethylamino)ethoxy]benzenemethanamine

HRID 1020742ノート

反応式

HRID 1020742 の反応式
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>C1COCC1>[NH2:10][CH2:9][C:8]1[CH:7]=[C:6]([CH:13]=[CH:12][CH:11]=1)[O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:14]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22343137HCID 22343137、化合物

生成物 1

HCID 167712843-[2-(Dimethylamino)ethoxy]benzenemethanamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
2.5 °C

実験手順

3-(2-Dimethylamino-ethoxy)-benzonitrile (0.8 g, 1 eq, 4.1 mmol) was dissolved in THF (80 mL) and cooled down to 0-5° C. A 1.0 M solution of lithium aluminium hydride in THF (0.47 g, 3.0 eq, 12.3 mmol) was added at 0-5° C. The reaction mixture was allowed to warm to RT and was stirred for 4 hrs. After completion of the reaction (confirmed by TLC), ethyl acetate at 0-5° C. was slowly added to quench any excess of lithium aluminium hydride in the reaction mixture, followed by addition of saturated sodium sulphate solution (2 mL). The reaction mass was filtered through hy-flow bed and the filtrate was concentrated in vacuo to obtain the crude product.

後処理

  1. temperatureto warm to RT
  2. additionwas slowly added
  3. customto quench any excess of lithium aluminium hydride in the reaction mixture
  4. additionfollowed by addition of saturated sodium sulphate solution (2 mL)
  5. filtrationThe reaction mass was filtered through hy-flow bed
  6. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-01cf25dcdb7343698430e9ed08b382dd
出典データセット
uspto-grants-2014_05
特許番号
US08716473B2

反応ノート

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