Water → HCID 18510779, compound

HRID 1370557Notes

Reaction equation

HRID 1370557 reaction equation
[N:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][NH:13][C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.O>CN(C)C=O>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:16]=[C:15]4[C:10]([CH2:11][CH2:12][NH:13][C:14]4=[O:17])=[CH:9][CH:8]=3)[CH2:2][CH2:3]2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 10609567HCID 10609567, compound

Product 1

HCID 18510779HCID 18510779, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Piperazin-1-yl-3,4-dihydro-2H-isoquinolin 1-one (100 mg) synthesized according to the method described in J. Med. Chem., 39, 4583 (1996) was dissolved in N, N-dimethylformamide (5 ml). Potassium carbonate (71 mg) and 4-chloro benzyl bromide (106 mg) were added to the solution. The mixture was stirred at room temperature for 2 hr. Water was added to the reaction solution. The mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=9:1) to give 7-[4-(4-chlorobenzyl)piperazin-1-yl]-3,4-dihydro-2H-isoquinolin-1-one (75 mg).

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was then removed by distillation under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-8fdebdca95cc4994bec453eddcf90246
Source dataset
uspto-grants-2003_06
Patent number
US06583144B2

Reaction notes

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