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

HRID 1251253Notes

Reaction equation

HRID 1251253 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+].[Li].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 3028194LithiumHCID 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 aluminumhydride (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-ce77402fd27146e080eba6f2db7fe9b2
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

Loading…