Water → 1-(4-Ethylpiperazin-1-yl)3-[4-(1,3-dioxolan-2-ylmethyloxy)phenyl]isoquinoline

HRID 1814521Notes

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]([OH:25])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH:34]1[O:38][CH2:37][CH2:36][O:35]1.O>CN(C)C=O>[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]([O:25][CH2:33][CH:34]4[O:38][CH2:37][CH2:36][O:35]4)=[CH:23][CH:24]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-(4-hydroxyphenyl)isoquinoline (0.53 g) was dissolved in N,N-dimethylformamide (5 ml), to which were added potassium carbonate (0.24 g) and 2-bromomethyl-1,3-dioxolane (250 ml), and the mixture was stirred at 90° C. overnight. Water was added to the reaction solution, and then the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 0.47 g of the title compound as a pale yellow oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record: ord-4958ba71665a4f2bac24a543292f6bf9
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875761B2

Reaction notes

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