p-Fluoronitrobenzene → 1,2,3,6-Tetrahydro-1-(4-nitrophenyl)-4-phenylpyridine

HRID 1452779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452779
[C:1]1([C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.C([O-])([O-])=O.[K+].[K+].F[C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[N+:35]([C:32]1[CH:33]=[CH:34][C:29]([N:10]2[CH2:9][CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)=[CH:30][CH:31]=1)([O-:37])=[O:36]

Komponenten

7

Edukt 5

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 47810351,2,3,6-Tetrahydro-1-(4-nitrophenyl)-4-phenylpyridineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 0.5 g (2.5 mmole) of 4-phenyl-1,2,3,6-tetrahydropyridine, 0.51 ml (2.8 mmole) of diisopropylethylamine, 0.71 g (5 mmole) of K2CO3, 0.40 g ((2.8 mmole) of 4-fluoronitrobenzene in 10 ml of DMF is heated at 100° C., for 24 hours. At the end of the reaction, the mixture is poured into 25 ml of a saturated solution of NaHCO3 and the product is extracted using 25 ml of AcOEt. After decantation, the organic solution is washed twice with 20 ml of water followed by 20 ml of brine, drying over magnesium sulphate, filtration and evaporation of the solvent under vacuum produce a yellow solid with a yield of 42%. Melting point: 185-192° C. (decomposition).

Aufarbeitung

  1. customAt the end of the reaction
  2. extractionthe product is extracted
  3. washAfter decantation, the organic solution is washed twice with 20 ml of water
  4. dry with materialdrying over magnesium sulphate, filtration and evaporation of the solvent under vacuum
  5. customproduce a yellow solid with a yield of 42%

Quellen und Nachweise

ORD-Eintrag
ord-3438d1070b8c492aa63396454fd34f3e
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473779B2

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