Potassium Carbonate → 1-(4-Ethylpiperazin-1-yl)-3-(4-methoxyphenyl)isoquinoline

HRID 1006872Notes

Reaction equation

HRID 1006872 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1.[CH2:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:20]([N:22]1[CH2:27][CH2:26][N:25]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[N:3]=2)[CH2:24][CH2:23]1)[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinoline

Product 1

HCID 99501681-(4-Ethylpiperazin-1-yl)-3-(4-methoxyphenyl)isoquinolineYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-chloro-3-(4-methoxyphenyl)isoquinoline (0.89 g), N-ethylpiperazine (0.86 g) and potassium carbonate (1.10 g) was heated in dimethylformamide (20 ml) at 90° C. for 12 hr. The reaction mixture was evaporated, water was added to the resulting residue, and then it was extracted with ethyl acetate. The resulting organic layer was washed with water and brine, dried over magnesium sulfate, and then the solvent was removed. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the tilte compound as a pale brown oil (1.02 g, yield; 88%).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater was added to the resulting residue
  3. extractionit was extracted with ethyl acetate
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed
  7. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-5f5df4ee914342c3b1665e484bfc8628
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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