Ethyl Acetate → 1-(4-Ethylpiperazin-1-yl)-7-methoxy-3-(2-methoxyphenyl)isoquinoline dihydrochloride

HRID 1006915Notes

Reaction equation

HRID 1006915 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[N:3]=1.[CH2:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[CH3:23].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[ClH:1].[ClH:1].[CH2:22]([N:24]1[CH2:29][CH2:28][N:27]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=3)[CH:5]=[C:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[N:3]=2)[CH2:26][CH2:25]1)[CH3:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 225036211-Chloro-7-methoxy-3-(2-methoxyphenyl)isoquinoline

Product 1

HCID 225029281-(4-Ethylpiperazin-1-yl)-7-methoxy-3-(2-methoxyphenyl)isoquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Chloro-7-methoxy-3-(2-methoxyphenyl)isoquinoline (0.56 g) was reacted with N-ethylpiperazine (5 ml) and potassium carbonate (0.5 g) at 120° C. for 5 hr. To the resulting reaction solution were added ethyl acetate and water, and then it was extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 0.43 g of the free compound of the title compound as a pale yellow oil.

Workup

  1. customTo the resulting reaction solution
  2. extractionit was extracted with ethyl acetate
  3. washThe resulting organic layer was washed with water 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 (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-04df4cca83b04b718c6ecb19ded9d024
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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