Ethyl isocyanate → HCID 22502549, compound

HRID 1814456Notes

Reaction equation

HRID 1814456 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](O)=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH2:26]([N:28]=[C:29]=[O:30])[CH3:27]>O1CCCC1>[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:24]=[CH:23][C:22]([C:29](=[O:30])[NH:28][CH2:26][CH3:27])=[CH:21][CH:20]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 1357190421-(1-Ethylpiperazin-4-yl)-3-(4-hydroxyphenyl)isoquinoline

Product 1

HCID 22502549HCID 22502549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(1-Ethylpiperazin-4-yl)-3-(4-hydroxyphenyl)isoquinoline (333 mg) was dissolved in tetrahydrofuran (5 ml), ethyl isocyanate (800 ml) was added thereto, and then the mixture was stirred at room temperature for 3 hr. The reaction mixture was evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), and then recrystallized from ethyl acetate/hexane, to give the free compound of the title compound. The free compound was converted into a hydrochloride in a conventional manner, which was then recrystallized (from ethanol/isopropyl ether), to give the hydrochloride of the title compound as yellow crystals (313 mg, yield; 70%).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)
  3. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-28216833a9004aa5bf2222fc9541a695
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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