Water → HCID 22502506, compound

HRID 1814522Notes

Reaction equation

HRID 1814522 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O>CN(C)C=O>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1357190421-(1-Ethylpiperazin-4-yl)-3-(4-hydroxyphenyl)isoquinoline

Product 1

HCID 22502506HCID 22502506, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-(4-hydroxyphenyl)isoquinoline (0.57 g) was dissolved in N,N-dimethylformamide (5 ml), to which were added potassium carbonate (0.24 g) and ethyl bromoacetate (210 ml), and the mixture was stirred at room temperature for 2 days. Water was added to the reaction solution, followed by the extraction with ethyl acetate. The extract 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 (chloroform/methanol system), to give obtain 1-(4-ethylpiperazin-1-yl)-3-[4-(ethoxycarbonylmethoxy)phenyl]isoquinoline (0.57 g) as a pale yellow viscous oil.

Workup

  1. extractionfollowed by the extraction with ethyl acetate
  2. washThe extract 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 (chloroform/methanol system)
  6. customto give

Sources & evidence

ORD record
ord-cd65b837d4184571bbdbc3763220b7aa
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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