Potassium Carbonate → 3-Methoxybenzamide

HRID 1069282

Reaktionsgleichung

Reaktionsgleichung von HRID 1069282
FC1C=CC2C(C3CCNCC3)=NOC=2C=1.C([O-])([O-])=O.[K+].[K+].BrCCCO[C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH2:34])=[O:33])=[CH:30][C:29]=1[O:37][CH3:38]>C(#N)C>[CH3:38][O:37][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:28]=1)[C:32]([NH2:34])=[O:33]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 101081354-(3-Bromopropoxy)3-methoxybenzamide

Produkt 1

HCID 984873-Methoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.2 g, 10.0 mmol), K2CO3 (2.0 g) and 4-(3bromopropoxy)-3-methoxybenzamide (2.32 g, 8.0 mmol) in acetonitrile (80 ml) was heated at reflux for 5 hours. At the end of the reaction the solvent was evaporated. The residue was extracted into dichloromethane. The inorganic insolubles were filtered off. The dichloromethane was concentrated again. The crude residue was purified by flash chromatography over a silica gel column (55 g, SiO2; eluted with 1% methanol in dichloromethane, 1 l; 2% methanol in dichloromethane, 1 l). The material thus obtained weighed 2.93 g (84%) as white crystals. Recrystallization from hot ethanol (60 ml) gave 2.2 g of 4-[3-4(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzamide as white crystals, m.p.=163-164° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customAt the end of the reaction the solvent
  4. customwas evaporated
  5. extractionThe residue was extracted into dichloromethane
  6. filtrationThe inorganic insolubles were filtered off
  7. concentrationThe dichloromethane was concentrated again
  8. customThe crude residue was purified by flash chromatography over a silica gel column (55 g, SiO2; eluted with 1% methanol in dichloromethane, 1 l; 2% methanol in dichloromethane, 1 l)
  9. customThe material thus obtained
  10. customRecrystallization from hot ethanol (60 ml)

Quellen und Nachweise

ORD-Eintrag
ord-09290611e2264a9f876fe2e4a23d33b8
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251907B1

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