HCID 19094075, compound → HCID 19898622, compound

HRID 1196468Notes

Reaction equation

HRID 1196468 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][CH2:14][N:15]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[C:16](=O)[CH3:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[CH2:16]([N:15]([CH2:14][CH2:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1)[CH3:17]

Participants

4

Reactant 2

HCID 19094075HCID 19094075, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19898622HCID 19898622, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 0.59 g of lithium aluminum hydride in 100 mL of dry ether was added, dropwise, a solution of 2.3 g of N-(2-phenylethyl)-N-(4-quinolinyl)acetamide dissolved in 50 mL of dry ether. The mixture was heated to reflux for seven hours. Excess lithium aluminum hydride was then destroyed by adding 100 mL of water to the mixture. The solvent was then removed, and the residue was dissolved in chloroform. After washing with water, the mixture was then dried and concentrated. Using HPLC (silica gel, CH2Cl2 →EtOAc), 0.80 g of the title product was isolated. Yield 36.7%. M.P. oil.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for seven hours
  4. customExcess lithium aluminum hydride was then destroyed
  5. additionby adding 100 mL of water to the mixture
  6. customThe solvent was then removed
  7. dissolutionthe residue was dissolved in chloroform
  8. washAfter washing with water
  9. customthe mixture was then dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e9f15788868e4608a047bc7c38694848
Source dataset
uspto-grants-1992_05
Patent number
US05114939

Reaction notes

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