Sodium hydride → 4-chloro-1-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1H-pyrazole

HRID 1977253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977253
[Cl:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].Cl[CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH:17]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14]1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][CH2:18]2)[CH:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 275241H-Pyrazole, 4-chloro-HCID 98375831-(3-Chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 219978824-chloro-1-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1H-pyrazoleAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2.05 g (20 mmol of 4-chloropyrazole in dimethylformamide is added dropwise to a suspension of 1.0 g of NaH in dimethylformamide. The white suspension is heated for 30 minutes at 100° C. Cooling is carried out and 4.7 g (20 mmol) of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine, dissolved in dimethylformamide, are added. Heating is carried out at reflux for 2 hours. Evaporation to dryness is then carried out and the residue is extracted with chloroform, washed with water and dried with sodium sulfate. The resulting crude product is purified by chromatography on silica gel. 5.2 g (17.2 mmol) of 4-chloro-1-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1H-pyrazole are obtained.

Aufarbeitung

  1. temperatureCooling
  2. additionare added
  3. temperatureHeating
  4. temperatureat reflux for 2 hours
  5. customEvaporation to dryness
  6. extractionthe residue is extracted with chloroform
  7. washwashed with water
  8. dry with materialdried with sodium sulfate
  9. customThe resulting crude product is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3f2a71e7ad65413d8d2f641c454e417c
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06232329B1

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