1-(2-Hydroxyethyl)piperazine → 1-[4-(2-Hydroxyethyl)piperazin-1-yl]-3-(4-methoxyphenyl)isoquinoline dihydrochloride

HRID 1006920Notes

Reaction equation

HRID 1006920 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:1].[ClH:1].[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[N:3]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinoline

Product 1

HCID 225025351-[4-(2-Hydroxyethyl)piperazin-1-yl]-3-(4-methoxyphenyl)isoquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-chloro-3-(4-methoxyphenyl)isoquinoline (0.79 g) obtained in Example 10-2, 1-(2-hydroxyethyl)piperazine (0.6 g), and potassium carbonate (0.83 g) was reacted in dimethylformamide (10 ml) at 100° C. for 6 hr. The reaction mixture solution was evaporated. Ethyl acetate and water were added to the resulting residue. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the free compound of the title compound as a pale yellow oil.

Workup

  1. customThe reaction mixture solution was evaporated
  2. additionEthyl acetate and water were added to the resulting residue
  3. washThe resulting organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-42a20cb9d3a94c5c921ae8908fd177fc
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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