Hydrochloric Acid → 1-(4-Ethylpiperazin-1-yl)-3-[4-(2-hydroxyethyl)phenyl]isoquinoline dihydrochloride

HRID 1251222Notes

Reaction equation

HRID 1251222 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]([CH2:25][CH2:26][O:27]CC4C=CC=CC=4)=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[ClH:35]>CO.[Pd]>[ClH:35].[ClH:35].[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]([CH2:25][CH2:26][OH:27])=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 177943201-(4-Ethylpiperazin-1-yl)-3-[4-(2-benzyloxyethyl)phenyl]isoquinoline

Product 1

HCID 225029131-(4-Ethylpiperazin-1-yl)-3-[4-(2-hydroxyethyl)phenyl]isoquinoline dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-[4-(2-benzyloxyethyl)phenyl]isoquinoline (0.46 g) was converted into a hydrochloride in a conventional manner. The resulting hydrochloride was then dissolved in methanol (50 ml), followed by the addition of 10% palladium/carbon catalyst (0.10 g), and the catalytic reduction was conducted at atmospheric pressure overnight. The catalyst was filtered off, while the solvent was evaporated. Water was added thereto, followed by the addition of a 1N aqueous solution of sodium hydroxide to adjust to pH 8, and then the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and evaporated. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 0.24 g of the free compound of the title compound as a pale brown viscous oil.

Workup

  1. customwas conducted at atmospheric pressure overnight
  2. filtrationThe catalyst was filtered off, while the solvent
  3. customwas evaporated
  4. additionWater was added
  5. additionfollowed by the addition of a 1N aqueous solution of sodium hydroxide
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe solvent was evaporated
  11. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-8ef98dd05ac244ea9930c2143fa62ee7
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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