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

HRID 1090568

Reaktionsgleichung

Reaktionsgleichung von HRID 1090568
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 19796283N-{1-[p-(5-Isoquinolinesulfonyloxy)benzyl]-2-(4-oxopiperidino)ethyl)-N-methyl-5-isoquinolinesulfonamideAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6fa053d3be124172b1d16d31771d68f5
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081246

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