Water → 1-(4-Ethylpiperazin-1-yl)-3-phenacylisoquinoline

HRID 1814586Notes

Reaction equation

HRID 1814586 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](Br)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])[CH3:21].C(O[K])(C)(C)C.O>CS(C)=O.[Hg]>[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]([CH2:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:22])[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7410AcetophenoneHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 178418922HCID 178418922, compound

Product 1

HCID 225034511-(4-Ethylpiperazin-1-yl)-3-phenacylisoquinolineYield 89.1%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 1-(4-ethylpiperazin-1-yl)-3-bromoisoquinoline (1.00 g), acetophenone (1.50 g) and tert-butoxypotassium (1.40 g) in dimethyl sulfoxide (50 ml) was irradiated with light (450 W; mercury-vapor lamp) at room temperature for 5 hr. Water (200 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and then extracted with a 2N aqueous solution of hydrochloric acid (100 ml). The resulting aqueous layer was basified with sodium carbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed, to give 1-(4-ethylpiperazin-1-yl)-3-phenacylisoquinoline (1.0 g) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe resulting organic layer was washed with water and brine
  3. extractionextracted with a 2N aqueous solution of hydrochloric acid (100 ml)
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-01d36832457944b4adbd74ffb3411222
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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