Sodium Chloride → 1-(4-Ethylpiperazin-1-yl)-3-[4-(3-hydroxy-1-methylpropyl)phenyl]isoquinoline oxalate

HRID 1007000Notes

Reaction equation

HRID 1007000 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]([CH:25]([CH3:32])[CH2:26][C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Na+].[OH-:41].[Na+].[O:43]1CCCC1>O>[C:27]([OH:29])(=[O:28])[C:26]([OH:43])=[O:41].[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]([CH:25]([CH3:32])[CH2:26][CH2:27][OH:28])=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 225031761-(4-Ethylpiperazin-1-yl)-3-[4-(1-ethoxycarbonylpropan-2-yl)phenyl]isoquinoline

Product 1

HCID 225033171-(4-Ethylpiperazin-1-yl)-3-[4-(3-hydroxy-1-methylpropyl)phenyl]isoquinoline oxalate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Subsequently, the resulting 1-(4-ethylpiperazin-1-yl)-3-[4-(1-ethoxycarbonylpropan-2-yl)phenyl]isoquinoline (0.69 g) was dissolved in tetrahydrofuran (10 ml). The solution was added to a suspension of lithium aluminum hydride (0.12 g) in tetrahydrofuran (20 ml) under cooling with a cooler of sodium chloride and ice, and the mixture was stirred for another 20 min. Water (120 ml), a 5N aqueous solution of sodium hydroxide (120 ml) and water (360 ml) were added to the reaction solution in this order, and then the resulting precipitates were filtered off. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (toluene/acetone system), to give 0.32 g of the free compound of the title compound as a pale brown viscous oil.

Workup

  1. customthe resulting precipitates
  2. filtrationwere filtered off
  3. customThe solvent was evaporated
  4. customthe resulting residue was purified by silica gel column chromatography (toluene/acetone system)

Sources & evidence

ORD record
ord-fc27ca4a5dd24491b213b5e5b7bb949b
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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