Barium Carbonate → 4-(Tetrahydroquinolin-1-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-quinoline

HRID 585356Notes

Reaction equation

HRID 585356 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11](O)[CH2:10][CH2:9]1)=[O:7].I[Si](C)(C)C.[NH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[Ba+2]>C(Cl)(Cl)Cl>[N:29]1([CH:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([C:6](=[O:7])[C:5]3[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9][CH2:10]2)[C:38]2[CH:33]([CH2:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 10563Barium CarbonateHCID 694601,2,3,4-TetrahydroquinolineHCID 85247Trimethylsilyl iodideHCID 223392201-(3,4-Dimethoxybenzoyl)-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 697750134-(Tetrahydroquinolin-1-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-quinolineYield 37%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(3,4-Dimethoxybenzoyl)-1,2,3,4-tetrahydro-4-quinolinol (400 mg, 1.28 mmol) prepared in Reference Example 2 was dissolved in chloroform (10 ml), to which iodotrimethylsilane (638 mg, 3.19 mmol) was then added on ice and stirred for 2 hours. After the reaction mixture was concentrated, the residue was dissolved in THF (10 ml) and mixed with 1,2,3,4-tetrahydroquinoline (511 mg, 3.84 mmol) and barium carbonate (505 mg, 2.56 mmol), followed by stirring at room temperature for 48 hours. After the reaction mixture was filtered to remove insoluble products and concentrated, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/3) and the resulting eluate was recrystallized from diethyl ether-hexane to give the product of interest, i.e., 4-(tetrahydroquinolin-1-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-quinoline (202 mg, yield: 37%) as a white crystal.

Workup

  1. additionwas then added on ice
  2. concentrationAfter the reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in THF (10 ml)
  4. stirringby stirring at room temperature for 48 hours
  5. filtrationAfter the reaction mixture was filtered
  6. customto remove insoluble products
  7. concentrationconcentrated
  8. customthe resulting eluate was recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-be207e4b57204e6d829cc3347494e3f9
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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