Ethyl Acetate → 1(4-Ethylpiperazin-1-yl)-7-methoxy-3-phenylisoquinoline dihydrochloride

HRID 1251144Notes

Reaction equation

HRID 1251144 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][CH:15]=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+].C(OCC)(=O)C>O>[ClH:1].[ClH:1].[CH2:20]([N:22]1[CH2:27][CH2:26][N:25]([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][CH:15]=3)[N:3]=2)[CH2:24][CH2:23]1)[CH3:21]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 22503127HCID 22503127, compound

Product 1

HCID 225031101(4-Ethylpiperazin-1-yl)-7-methoxy-3-phenylisoquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Chloro-7-methoxy-3-phenylisoquinoline (0.20 g) was reacted with N-ethylpiperazine (3 ml) and potassium carbonate (0.2 g) at 120° C. for 5 hr. To the reaction solution were added ethyl acetate and water, and 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 0.18 g of the free compound of the title compound as a pale yellow oil.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe resulting organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-a73cf3a837e140a6aaf4785587e5f13a
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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