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Potassium Hydroxide → 4-(2,5-Dimethyl-4-nitrophenyl)-1-(4-methoxybenzyl)piperidin-2-one

HRID 1897691
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1897691
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.[CH3:21][O:22][C:23]1[CH:36]=[CH:35][C:26]([CH2:27][N:28]2[CH2:33][CH2:32][CH:31]=[CH:30][C:29]2=[O:34])=[CH:25][CH:24]=1.[OH-].[K+]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh].O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1[CH:31]1[CH2:32][CH2:33][N:28]([CH2:27][C:26]2[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:36][CH:35]=2)[C:29](=[O:34])[CH2:30]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 145643581-(4-Methoxybenzyl)-5,6-dihydropyridin-2(1H)-oneHCID 671555522-(2,5-Dimethyl-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 671553414-(2,5-Dimethyl-4-nitrophenyl)-1-(4-methoxybenzyl)piperidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6436379
Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 5 mL microwave reaction tube was added 2-(2,5-dimethyl-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (143 mg, 0.516 mmol, prepared from 1-bromo-2,5-dimethyl-4-nitrobenzene by standard protocol), 1-(4-methoxybenzyl)-5,6-dihydropyridin-2(1H)-one (56 mg, 0.26 mmol, prepared by following a similar procedure as reported by Lerchner etc. in Chem. Eur. J. 2006, 12, 8208), chloro(1,5-cyclooctadiene)rhodium (I) dimer (13 mg, 0.026 mmol), KOH (0.13 mL 1N aqueous solution) and dioxane (1.2 mL). The tube was degassed, filled with N2 and sealed. The reaction tube was then heated to 100° C. in a microwave reactor for 10 min. After the reaction tube was opened, the mixture was treated with saturated NH4Cl aqueous solution (3 mL) and extracted with EtOAc (3×4 mL). The organic layers were combined and concentrated. The residue was purified by flash column chromatography (silica gel, gradient 0%-70% EtOAc/hexane), to provide 4-(2,5-dimethyl-4-nitrophenyl)-1-(4-methoxybenzyl)piperidin-2-one. ESMS m/z 369.2 (M+H+).

Aufarbeitung

  1. customprepared
  2. customThe tube was degassed
  3. additionfilled with N2
  4. customsealed
  5. additionthe mixture was treated with saturated NH4Cl aqueous solution (3 mL)
  6. extractionextracted with EtOAc (3×4 mL)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (silica gel, gradient 0%-70% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cfc9811cd44a4b1fb100c31b886ee20c
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08519129B2

Notizen zur Reaktion

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