Sodium hydride → 1-Acetyl-4-ethynyl-4-(2-nitrophenoxy)piperidine

HRID 1193548

Reaktionsgleichung

Reaktionsgleichung von HRID 1193548
[Na+].CS([CH2-])=O.[H-].[Na+].[C:8]([N:11]1[CH2:16][CH2:15][C:14]([C:18]#[CH:19])([OH:17])[CH2:13][CH2:12]1)(=[O:10])[CH3:9].F[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>O.CS(C)=O>[C:8]([N:11]1[CH2:16][CH2:15][C:14]([C:18]#[CH:19])([O:17][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-:29])=[O:28])[CH2:13][CH2:12]1)(=[O:10])[CH3:9]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 10154010Methane, sulfinylbis-, ion(1-), sodiumHCID 132167351-(4-Ethynyl-4-hydroxypiperidin-1-yl)ethan-1-one

Produkt 1

HCID 142814881-Acetyl-4-ethynyl-4-(2-nitrophenoxy)piperidineAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of dimsyl sodium, prepared from 16.5 g of sodium hydride (50% in oil, washed three times with hexanes) and 400 ml of dimethylsulfoxide at 17°-25° was added, in aliquots, 57.7 g of 1-acetyl-4-ethynyl-4-piperidinol. Upon completion of the addition, 55.3 g of 2-fluoronitrobenzene was added dropwise at a rate such that the temperature remained below 25°. The mixture was stirred at room temperature for 20 min, poured into cold water, extracted three times with ether, washed with saturated sodium chloride solution and dried over anhydrous potassium carbonate. Filtration followed by evaporation of solvent provided an oil, which crystallized on standing. Recrystallization from ethyl acetate/cyclohexane provided 23.6 g (24%) of product, mp 112°-115°.

Aufarbeitung

  1. additionwas added dropwise at a rate such that the temperature
  2. customremained below 25°
  3. extractionextracted three times with ether
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationFiltration
  7. customfollowed by evaporation of solvent
  8. customprovided an oil, which
  9. customcrystallized
  10. customRecrystallization from ethyl acetate/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-3ebe733b3b70488daa38ed37d48b843b
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810792

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