Aluminium lithium hydride → 1-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amine

HRID 1922502노트

반응식

HRID 1922502 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:7](=O)[CH2:6][CH2:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[O:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][N:8]2[C:9]3[C:4](=[CH:3][C:2]([NH2:1])=[CH:11][CH:10]=3)[CH2:5][CH2:6][CH2:7]2)[CH2:15][CH2:16]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 434465466-amino-1-(2-morpholinoethyl)-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 284191151-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amine수율 36%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A mixture of compound 3 (0.800 g, 2.905 mmol) in THF (25 mL) was stirred at 0° C. and was treated with solid lithium aluminum hydride (0.4352 g, 11.62 mmol). The mixture was brought to room temperature at which point it was heated to reflux for 1 hour. The reaction was quenched with H2O (1 mL), 3N NaOH solution (1 mL) and an additional aliquot of H2O (1 mL). The solution was filtered over celite and was rinsed with diethyl ether. The concentrated crude product was subject to flash chromatography on silica gel 5% 2M NH3 methanol/CH2Cl2, which resulted in a dark brown viscous liquid, compound 4 (0.27 g, 36%).

후처리

  1. customwas brought to room temperature at which point it
  2. temperaturewas heated
  3. temperatureto reflux for 1 hour
  4. customThe reaction was quenched with H2O (1 mL), 3N NaOH solution (1 mL)
  5. filtrationThe solution was filtered over celite
  6. washwas rinsed with diethyl ether
  7. concentrationThe concentrated crude product

출처 및 근거

ORD 기록
ord-da27729340254f9497907b0dba577e02
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173813B2

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