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

HRID 1922502ノート

反応式

HRID 1922502 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-da27729340254f9497907b0dba577e02
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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