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

HRID 1251154Notes

Reaction equation

HRID 1251154 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-68c1874867f1456eb18dbd8a03b1ed9b
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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