1,2-Dibromoethane → 1-(4-Chlorocinnamyl)-4-(5-isoquinolinesulfonyl)piperazine

HRID 1090586Notes

Reaction equation

HRID 1090586 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH:6]=[CH:7][CH2:8][NH:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[C:17]3[CH:18]=[CH:19][N:20]=[CH:21][C:22]=3[CH:23]=[CH:24][CH:25]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.Br[CH2:29][CH2:30]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][N:9]2[CH2:30][CH2:29][N:12]([S:13]([C:16]3[C:17]4[CH:18]=[CH:19][N:20]=[CH:21][C:22]=4[CH:23]=[CH:24][CH:25]=3)(=[O:14])=[O:15])[CH2:11][CH2:10]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 176156N-[2-(4-Chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamide

Product 1

HCID 542037031-(4-Chlorocinnamyl)-4-(5-isoquinolinesulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.31 g of t product of Example 172 was dissolved in 3 ml of dimethylformamide, to the solution were added 644 mg of 1,2-dibromoethane and 1.13 g of anhydrous potassium carbonate at a room temperature, and the mixture was stirred for 24 hours. After adding 100 ml of ethyl acetate, the ethyl acetate layer was sequentially washed with water and a saturated sodium chloride aqueous solution twice in each case, and dried over magnesium sulfate. The solution was filtered and evaporated under a reduced pressure, and resulting residue was purified on a silica gel column (silica gel 50 g, eluant: 5% methanol in chloroform), to obtain 356 mg of the title compound in a colorless amorphous form, while recovering the residual starting material.

Workup

  1. washthe ethyl acetate layer was sequentially washed with water
  2. dry with materiala saturated sodium chloride aqueous solution twice in each case, and dried over magnesium sulfate
  3. filtrationThe solution was filtered
  4. customevaporated under a reduced pressure
  5. customresulting residue
  6. customwas purified on a silica gel column (silica gel 50 g, eluant: 5% methanol in chloroform)

Sources & evidence

ORD record
ord-2c674c8da3f34779851e966d67b57d19
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Reaction notes

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