p-Fluoronitrobenzene → Methyl 1-(4-nitrophenyl)piperidine-4-carboxylate

HRID 1691932

Reaktionsgleichung

Reaktionsgleichung von HRID 1691932
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:14].C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:11][O:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:17][CH2:16]1)=[O:14]

Komponenten

5

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 424914Methyl isonipecotate

Produkt 1

HCID 345002Methyl 1-(4-nitrophenyl)piperidine-4-carboxylateAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 4-fluoronitrobenzene (0.70 g, 4.96 mmol) in THF (8 mL) was added piperadine-4-carboxylic acid methyl ester (0.71 g, 4.96 mmol) and diisopropylethylamine (0.66 g, 5.11 mmol). The mixture was heated in a microwave oven at 150° C. for 1.5 hr. The resulting mixture was extracted with ethyl acetate and hydrochloric acid (0.2 N). The organic layer was washed with brine and concentrated sodium bicarbonate solution. After the evaporation of solvents, the residue was purified through a Biotage flash column chromatography using ethyl acetate and hexanes (1:1 ratio) to give a yellow solid as 1-(4-nitrophenyl)-piperidine-4-carboxylic acid methyl ester (490 mg). 1H-NMR is consistent with the structure.

Aufarbeitung

  1. extractionThe resulting mixture was extracted with ethyl acetate and hydrochloric acid (0.2 N)
  2. washThe organic layer was washed with brine and concentrated sodium bicarbonate solution
  3. customAfter the evaporation of solvents
  4. customthe residue was purified through a Biotage flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2e91b16b27d145648a4b459fad382340
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153644B2

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