Water → HCID 22502544, compound

HRID 1007007Notes

Reaction equation

HRID 1007007 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 compoundof 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-d131e39ffa804bccb0d9b67ac147781d
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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