Water → 1-(4-Ethylpiperazin-1-yl)-3-(2-hydroxymethylindan-5-yl)isoquinoline dihydrochloride

HRID 1814570Notes

Reaction equation

HRID 1814570 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:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[CH2:24][CH:23]([C:28](OCC)=[O:29])[CH2:22]4)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[Cl-:33].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[ClH:33].[ClH:33].[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]=[C:21]4[C:25](=[CH:26][CH:27]=3)[CH2:24][CH:23]([CH2:28][OH:29])[CH2:22]4)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 21226445Aluminium lithium hydrideHCID 225026151-(4-Ethylpiperazin-1-yl)-3-(2-ethoxycarbonylindan-5-yl)isoquinoline

Product 1

HCID 225025071-(4-Ethylpiperazin-1-yl)-3-(2-hydroxymethylindan-5-yl)isoquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-(2-ethoxycarbonylindan-5-yl)isoquinoline (1.06 g) was dissolved in tetrahydrofuran (6 ml). Under cooling with a cooler of sodium chloride and ice, the solution was added to a suspension of lithium aluminum hydride (0.10 g) in tetrahydrofuran (10 ml), and the mixture was stirred for 20 min. To the resulting solution were sequentially added water (100 ml), a 5N aqueous solution of sodium hydroxide (100 ml) and water (300 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 0.35 g of the free compound of the title compound as a pale yellow amorphous.

Workup

  1. customa 5N aqueous solution of sodium hydroxide (100 ml) and water (300 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-4d10f6cadf584880bcfe2f5dcc5a1a43
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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