Sodium Chloride → N-{1-[(3,4-Dibenzyloxyphenyl)methyl]-2-(4-phenylpiperazinyl)ethyl}-N-methyl-5-isoquinoline sulfonamide

HRID 5719Notes

Reaction equation

HRID 5719 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH:24]([NH:38][S:39]([C:42]2[C:43]3[CH:44]=[CH:45][N:46]=[CH:47][C:48]=3[CH:49]=[CH:50][CH:51]=2)(=[O:41])=[O:40])[CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:28][CH2:27]2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:54]I.[Cl-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH:24]([N:38]([CH3:54])[S:39]([C:42]2[C:43]3[CH:44]=[CH:45][N:46]=[CH:47][C:48]=3[CH:49]=[CH:50][CH:51]=2)(=[O:41])=[O:40])[CH2:25][N:26]2[CH2:27][CH2:28][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:30][CH2:31]2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19796262N-{1-[(3,4-Dibenzyloxyphenyl)methyl]-2-(4-phenylpiperazinyl)ethyl}-5-isoquinoline sulfonamide

Product 1

HCID 19796321N-{1-[(3,4-Dibenzyloxyphenyl)methyl]-2-(4-phenylpiperazinyl)ethyl}-N-methyl-5-isoquinoline sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

470 mg of the amorphous compound obtained in Example 5 was dissolved in 8 ml of dimethylformamide, and to the solution were sequentially added 30 mg of 60% sodium hydride and 0.1 ml of methyl iodide with ice cooling, and after stirring for two hours with ice cooling was added saturated sodium chloride, and the mixture was extracted with 50 ml of ethyl acetate. The extract was washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate and concentrated under a reduced pressure to obtain a residue, which was then applied to a silica gel column and eluted with hexane/ethyl acetate (1:1) to obtain 413 mg of the title compound in a colorless amorphous form.

Workup

  1. extractionthe mixture was extracted with 50 ml of ethyl acetate
  2. washThe extract was washed with saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customto obtain a residue, which
  6. washeluted with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-2441e4247d98489c8f8cd66875c8b08f
Source dataset
uspto-grants-1993_09
Patent number
US05245034

Reaction notes

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