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

HRID 1007027Notes

Reaction equation

HRID 1007027 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-1c1471c6455c49889abd8320b8554c8d
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

Loading…