Water → HCID 135719041, compound

HRID 1814439Notes

Reaction equation

HRID 1814439 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([O:24]CC(OCC)=O)=[CH:20][CH:19]=3)[N:9]=2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[N:9]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22502896HCID 22502896, compound

Product 1

HCID 135719041HCID 135719041, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1-Methylpiperazin-4-yl)-3-[4-(ethoxycarbonylmethoxy)phenyl]isoquinoline (320 mg) was dissolved in tetrahydrofuran (5 ml), to which was added lithium aluminium hydride (16 mg) under ice-cooling, followed by stirring for 5 min. To the resulting reaction mixture were then added water (16 ml), 5N sodium hydroxide (16 ml) and water (48 ml) in this order. After diluting with ethyl acetate, it was filtered through Celite and evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), which was converted into a hydrochloride in a conventional manner, and then recrystallized from in ethanol, to give the hydrochlroide of the title compound as yellow crystals (105 mg, yield; 50%).

Workup

  1. temperaturecooling
  2. customTo the resulting reaction mixture
  3. filtrationwas filtered through Celite
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), which
  6. customrecrystallized from in ethanol

Sources & evidence

ORD record
ord-123e1415f2ae4d458dbcd9524b1cf98c
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

Loading…