HCID 19919390, compound → 1,2,3,4-tetrahydro-8-(aminomethyl)-N,N-dipropyl-3-quinolinamine

HRID 1648325Notes

Reaction equation

HRID 1648325 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:10]([CH2:25][CH2:26][CH3:27])[CH:11]1[CH2:20][C:19]2[C:14](=[C:15]([C:21]([NH2:23])=O)[CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=O)[CH2:8][CH3:9]>C1COCC1>[NH2:23][CH2:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[NH:13][CH2:12][CH:11]([N:10]([CH2:25][CH2:26][CH3:27])[CH2:7][CH2:8][CH3:9])[CH2:20]2

Participants

4

Reactant 2

HCID 19919390HCID 19919390, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 157449971,2,3,4-tetrahydro-8-(aminomethyl)-N,N-dipropyl-3-quinolinamineYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.5 g) was added to a stiffed solution of 3-(dipropylamino)-1,2, 3,4-tetrahydro-2-oxo-8-quinolinecarboxamide (0.75 g) in THF (125 mL) and the solution was refluxed for 2 days. The solution was cooled and excess hydride was destroyed by addition of methanol (20 mL) and the solvents were removed under reduced pressure. The residue was partitioned between ethyl acetate (400 mL) and water (15 mL). The ethyl acetate was decanted from the inorganic solids and the solvent removed under reduced pressure. The residual oil was dissolved in chloroform and chromatographed on silica gel. Elution of the column with 5% methanol:chloroform gave 0.40 g of 1,2,3,4-tetrahydro-8-(aminomethyl)-N,N-dipropyl-3-quinolinamine.

Workup

  1. temperaturethe solution was refluxed for 2 days
  2. temperatureThe solution was cooled
  3. customexcess hydride was destroyed by addition of methanol (20 mL)
  4. customthe solvents were removed under reduced pressure
  5. customThe residue was partitioned between ethyl acetate (400 mL) and water (15 mL)
  6. customThe ethyl acetate was decanted from the inorganic solids
  7. customthe solvent removed under reduced pressure
  8. dissolutionThe residual oil was dissolved in chloroform
  9. customchromatographed on silica gel
  10. washElution of the column with 5% methanol

Sources & evidence

ORD record
ord-8e198412e9b94d2c8450ad1627d82673
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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