Hydrochloric Acid → 1-Methyl-4-ethynyl-4-(2-nitrophenoxy)piperidine hydrochloride

HRID 1193546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193546
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][C:7]([C:11]#[CH:12])([OH:10])[CH2:6][CH2:5]1.F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].[ClH:23]>CS(C)=O.O>[ClH:23].[CH3:3][N:4]1[CH2:9][CH2:8][C:7]([C:11]#[CH:12])([O:10][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])[CH2:6][CH2:5]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 14190994-Ethynyl-1-methylpiperidin-4-ol

Produkt 1

HCID 212725931-Methyl-4-ethynyl-4-(2-nitrophenoxy)piperidine hydrochlorideAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A suspension of 0.58 g of sodium hydride (59% in oil; washed three times with hexanes) in 15 ml of dimethylsulfoxide was heated at 80°-90° for 0.5 hour under nitrogen. The resultant solution was cooled in an ice bath and 2.0 g of 1-methyl-4-ethynyl-4-hydroxypiperidine was added. After five min, the mixture was cooled to 0° and a solution of 2.4 g of 2-fluoronitrobenzene was added dropwise. The mixture was stirred 1 hr at 0°, 3 hrs at room temperature, poured into water, extracted twice with ether, washed with saturated sodium chloride solution and dried over anhydrous potassium carbonate. Filtration followed by evaporation of the solvent provided an oil, which was treated with ethereal hydrogen chloride to yield 2.34 g (54.8%) of product.

Aufarbeitung

  1. temperaturewas heated at 80°-90° for 0.5 hour under nitrogen
  2. temperaturethe mixture was cooled to 0°
  3. extractionextracted twice with ether
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationFiltration
  7. customfollowed by evaporation of the solvent
  8. customprovided an oil, which

Quellen und Nachweise

ORD-Eintrag
ord-b660e4bfff8b4b6d84b85f0a85e8155e
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810792

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