Epichlorohydrin → 9-Methoxy-6-[4-(oxiran-2-ylmethyl)piperazin-1-yl]-11h-indeno[1,2-c]quinolin-11-one

HRID 1170880Notes

Reaction equation

HRID 1170880 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]2[C:8]3[C:9]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)=[N:10][C:11]4[C:16]([C:7]=3[C:6](=[O:26])[C:5]=2[CH:4]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4.[H-].[Na+].[CH2:29]([CH:31]1[O:33][CH2:32]1)Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]2[C:8]3[C:9]([N:17]4[CH2:22][CH2:21][N:20]([CH2:29][CH:31]5[CH2:32][O:33]5)[CH2:19][CH2:18]4)=[N:10][C:11]4[C:16]([C:7]=3[C:6](=[O:26])[C:5]=2[CH:4]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 242059869-Methoxy-6-(piperazin-1-yl)-11H-indeno[1,2-c]quinolin-11-one

Product 1

HCID 875667359-Methoxy-6-[4-(oxiran-2-ylmethyl)piperazin-1-yl]-11h-indeno[1,2-c]quinolin-11-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 5x (0.35 g, 1 mmol, obtained from the above Synthesis Example 12) in dry DMF (20 mL) was added NaH (60% in oil, 2.64 g, 66.0 mmol) at 0° C. for 1 hr. After stirring at room temperature for 8 hrs, epichlorohydrin (0.92 g, 10 mmol) was added and stirred for a further 1 hr. The reaction mixture was partitioned between H2O and CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The resultant residue was purified by column chromatography (MeOH/CH2Cl2=1:10) to give the title compound 5kkk (0.33 g, 84% yield).

Workup

  1. stirringstirred for a further 1 hr
  2. customThe reaction mixture was partitioned between H2O and CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe resultant residue was purified by column chromatography (MeOH/CH2Cl2=1:10)

Sources & evidence

ORD record
ord-3e69b72f9415437f8fe2790b15f26159
Source dataset
uspto-grants-2010_11
Patent number
US07829567B2

Reaction notes

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