Hydrochloric Acid → HCID 135719057, compound

HRID 1814547Notes

Reaction equation

HRID 1814547 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]=[C:23]([F:25])[C:22]([O:26]CC4C=CC=CC=4)=[C:21]([F:34])[CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].Cl>CO.[Pd]>[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]=[C:23]([F:25])[C:22]([OH:26])=[C:21]([F:34])[CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 22503215HCID 22503215, compound

Product 1

HCID 135719057HCID 135719057, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-(4-benzyloxy-3,5-difluorophenyl)isoquinoline (6.44 g) was converted into a hydrochloride in a conventional manner. The hydrochloride was dissolved in methanol (200 ml), followed by the addition of 10% palladium/carbon catalyst (0.48 g), and then the catalytic reduction was conducted at atmospheric pressure overnight. The catalyst was filtered off, while the solvent was evaporated. Water was added to the resulting residue, followed by the addition of an aqueous solution of saturated sodium bicarbonate, and the mixture was extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate, and the solvent was evaporated, to give obtain 1-(4-ethylpiperazin-1-yl)-3-(3,5-difluoro-4-hydroxyphenyl)isoquinoline (3.36 g) as a pale brown amorphous.

Workup

  1. customwas conducted at atmospheric pressure overnight
  2. filtrationThe catalyst was filtered off, while the solvent
  3. customwas evaporated
  4. additionWater was added to the resulting residue
  5. additionfollowed by the addition of an aqueous solution of saturated sodium bicarbonate
  6. extractionthe mixture was extracted with chloroform
  7. washThe extract was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent was evaporated
  10. customto give

Sources & evidence

ORD record
ord-d60373771145431c91c15e48c9c4cb8e
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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