Sodium Hydroxide → HCID 57652402, Verbindung

HRID 1930217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930217
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[NH:14][CH:13]=[CH:12]3)[CH2:4][CH2:3]1.[Cl:20]N1C(=O)CCC1=O.[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:20][C:10]1[C:9]([O:8][CH:5]2[CH2:4][CH2:3][NH:2][CH2:7][CH2:6]2)=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][NH:14][C:15]2=[O:19]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 426359186-[(Piperidin-4-yl)oxy]isoquinolin-1(2H)-one--hydrogen chloride (1/1)

Produkt 1

HCID 57652402HCID 57652402, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

60 mg (0.21 mmol) 6-(piperidin-4-yloxy)-2H-isoquinolin-1-one-hydrochloride (12) were dissolved in 5 mL of concentrated sulphuric acid. At 0° C. 28.6 mg (0.21 mmol) of N-chloro succinimide were added and the mixture was stirred at 50° C. After 2 h the solution was poured on ice and the pH was brought to about 12 by adding solid NaOH. The aqueous solution was extracted twice with dichloromethane. The organic layers were dried with MgSO4 and evaporated. The crude product was purified by preparative HPLC. The obtained trifluoroacetate was dissolved in 2 N HCl and the solvent was removed i. vac. Dissolving the residue in water, followed by lyophilization gave the desired product as HCl-salt. Rt=0.86 min (Method A). Detected mass: 279.1/281.1 (M+H+).

Aufarbeitung

  1. customAt 0° C
  2. additionAfter 2 h the solution was poured on ice
  3. extractionThe aqueous solution was extracted twice with dichloromethane
  4. dry with materialThe organic layers were dried with MgSO4
  5. customevaporated
  6. customThe crude product was purified by preparative HPLC
  7. dissolutionThe obtained trifluoroacetate was dissolved in 2 N HCl
  8. customthe solvent was removed i
  9. dissolutionDissolving the residue in water

Quellen und Nachweise

ORD-Eintrag
ord-0b095eb88b64451289ef1d7b099b0f89
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188117B2

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