Water → HCID 22502544, compound

HRID 1814566Notes

Reaction equation

HRID 1814566 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][C:26]([C:29]([O:31]C)=[O:30])([CH3:28])[CH3:27])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Na+].[OH2:41].[O:42]1CCCC1>>[C:29]([OH:31])(=[O:30])[C:26]([OH:42])=[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]([CH2:25][C:26]([CH3:27])([CH3:28])[CH2:29][OH:30])=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 5234Sodium ChlorideHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 22503665HCID 22503665, compound

Product 1

HCID 22502544HCID 22502544, compound

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-[4-(2-methoxycarbonyl-2-methylpropyl)phenyl]isoquinoline (1.51 g) was dissolved in tetrahydrofuran (10 ml). The solution was added to a suspension of lithium aluminum hydride (0.14 g) in tetrahydrofuran (20 ml) under cooling with a cooler of sodium chloride and ice, and the mixture was stirred for another 30 min. To the resulting solution were sequentially added water (140 ml), a 5N aqueous solution of sodium hydroxide (140 ml) and water (420 ml), and 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 0.90 g of the free compound of the title compound as a pale brown viscous oil.

Workup

  1. customa 5N aqueous solution of sodium hydroxide (140 ml) and water (420 ml), and the 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-af1cb6cb69cf43e58aa9de5ad8d9fc4c
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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