Potassium Carbonate → 3,5-Dimethyl-1-(3-Methyl-4-Nitrobenzyl)piperidine

HRID 1500174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500174
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Br.[CH3:13][CH:14]1[CH2:19][CH:18]([CH3:20])[CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:13][CH:14]1[CH2:19][CH:18]([CH3:20])[CH2:17][N:16]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=2)[CH2:15]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1182593,5-DimethylpiperidineHCID 44459783-Methyl-4-nitrobenzyl bromide

Produkt 1

HCID 533585523,5-Dimethyl-1-(3-Methyl-4-Nitrobenzyl)piperidineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3-Methyl-4-nitrobenzyl bromide (1.00 g), 3,5-dimethylpiperidine (0.60 ml) and potassium carbonate (0.90 g) were dissolved in acetone (20 ml), followed by heating under reflux for 6 hours. The reaction solution was concentrated under reduced pressure, dissolved in chloroform (10 ml), poured into water (100 ml) and extracted with chloroform (50 ml). The organic layer was washed with saturated brine (100 ml), dried over anhydrous sodium sulfate and, after filtration, concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (developing solvent: n-hexane/ethyl acetate=10:1) to obtain the subject compound (NCR-7) (0.70 g, yield 61%) as a yellow oil.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. dissolutiondissolved in chloroform (10 ml)
  5. additionpoured into water (100 ml)
  6. extractionextracted with chloroform (50 ml)
  7. washThe organic layer was washed with saturated brine (100 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationafter filtration
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane/ethyl acetate=10:1)
  12. customto obtain the subject compound (NCR-7) (0.70 g, yield 61%) as a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-2b9d2d25a2154c028c5f4e8e61c44dbe
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206125B2

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