Sodium Bicarbonate → N-{1-[p-(5-Isoquinolinesulfonyloxy)benzyl]-2-(4-oxopiperidino)ethyl)-N-methyl-5-isoquinolinesulfonamide

HRID 1090568Notes

Reaction equation

HRID 1090568 reaction equation
C1CO[C:3]2([CH2:8][CH2:7][N:6]([CH2:9][CH:10]([N:32]([CH3:46])[S:33]([C:36]3[C:37]4[CH:38]=[CH:39][N:40]=[CH:41][C:42]=4[CH:43]=[CH:44][CH:45]=3)(=[O:35])=[O:34])[CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][S:19]([C:22]4[C:23]5[CH:24]=[CH:25][N:26]=[CH:27][C:28]=5[CH:29]=[CH:30][CH:31]=4)(=[O:21])=[O:20])=[CH:14][CH:13]=3)[CH2:5][CH2:4]2)[O:2]1.C(=O)(O)[O-].[Na+]>Cl>[CH:27]1[C:28]2[CH:29]=[CH:30][CH:31]=[C:22]([S:19]([O:18][C:15]3[CH:14]=[CH:13][C:12]([CH2:11][CH:10]([N:32]([CH3:46])[S:33]([C:36]4[C:37]5[CH:38]=[CH:39][N:40]=[CH:41][C:42]=5[CH:43]=[CH:44][CH:45]=4)(=[O:34])=[O:35])[CH2:9][N:6]4[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]4)=[CH:17][CH:16]=3)(=[O:20])=[O:21])[C:23]=2[CH:24]=[CH:25][N:26]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 53669357N-{2-(4,4-ethylenedioxypiperidino)-1-[p-(5-isoquinolinesulfonyloxy)benzyl]ethyl}-N-methyl-5-isoquinolinesulfonamide

Product 1

HCID 19796283N-{1-[p-(5-Isoquinolinesulfonyloxy)benzyl]-2-(4-oxopiperidino)ethyl)-N-methyl-5-isoquinolinesulfonamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2.57 g of the product of Example 94 was dissolved in 50 ml of 3 N hydrochloric acid, and after refluxing for 6 hours and then cooling, the reaction mixture was alkalized with saturated sodium bicarbonate aqueous solution and extracted twice with 200 ml of chloroform. The extract was dried over magnesium sulfate and evaporated under a reduced pressure to remove the solvent, and resulting residue was applied to a silica gel column and eluted with chloroform/methanol (50:1) to obtain 2.22 g of the title compound in a colorless amorphous form.

Workup

  1. temperatureafter refluxing for 6 hours
  2. temperaturecooling
  3. extractionextracted twice with 200 ml of chloroform
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customevaporated under a reduced pressure
  6. customto remove the solvent
  7. customresulting residue
  8. washeluted with chloroform/methanol (50:1)

Sources & evidence

ORD record
ord-6fa053d3be124172b1d16d31771d68f5
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Reaction notes

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