Dimethylformamide → HCID 22502805, compound

HRID 1814574Notes

Reaction equation

HRID 1814574 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:28].CN(C)C=O>O>[ClH:1].[ClH:1].[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:32]2[CH2:33][CH2:34][N:29]([CH2:27][CH3:28])[CH2:30][CH2:31]2)=[N:3][C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 791961-Ethylpiperazine3×HCID 22503395HCID 22503395, compound

Product 1

HCID 22502805HCID 22502805, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the resulting 1,4-dichloro-3-(4-methoxyphenyl)isoquinoline (0.30 g) were added potassium carbonate (0.14 g), N-ethylpiperazine (126 ml) and N,N-dimethylformamide (10 ml). The resulting mixture was stirred at room temperature overnight. To the mixture was then added N-ethylpiperazine (126 ml), and the mixture was stirred at room temperature for 4 hr. Still additionally, N-ethylpiperazine (378 ml) was added thereto, and the mixture was stirred at 50° C. for 1.5 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed sequentially with water (four times) and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/acetone system), to give 0.10 g of the free compound of the title compound as a colorless viscous oil.

Workup

  1. stirringthe mixture was stirred at 50° C. for 1.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed sequentially with water (four times) and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/acetone system)

Sources & evidence

ORD record
ord-dcc1b88feb4f4d00b00abd5b2a652ffa
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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