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

HRID 1020742노트

반응식

HRID 1020742 반응식
[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]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22343137HCID 22343137, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
2.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-01cf25dcdb7343698430e9ed08b382dd
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716473B2

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