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

HRID 1922502Notes

Reaction equation

HRID 1922502 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-da27729340254f9497907b0dba577e02
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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