4-Nitrobenzoic Acid → 1-(4-Nitrobenzoyl)piperidine

HRID 1744346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744346
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:10])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 61084-Nitrobenzoic AcidHCID 8082PiperidineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2254681-(4-Nitrobenzoyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A room temperature solution of 5.04 gms. 4-nitro-benzoic acid in tetrahydrofuran (10 mL) is treated with 5.14 gms. 1′,1′-carbonyl-diimidizole and immediately immersed in an ice bath. The reaction mixture is stirred in the ice bath for 30 minutes, then it is allowed to warm to room temperature. Once at room temperature the reaction mixture is treated with 3 mL piperidine. The reaction mixture is allowed to stir at room temperature ovenight. The reaction is then made basic with the addition of saturated aqueous sodium bicarbonate solution, and the resulting mixture is extracted with ethyl acetate. The organics are separated, dried over anhydrous sodium sulfate, and subsequently evaporated to dryness in vacuo. The crude product residue is then chromatographed by flash silica gel chromatography using 50% ethyl acetate in hexanes as the eluant. Following evaporation of solvent, 1-(4-nitrobenzoyl)piperidine is isolated as a white solid in the amount of 5.87 gms.

Aufarbeitung

  1. customA room temperature solution of 5.04 gms
  2. custom1′,1′-carbonyl-diimidizole and immediately immersed in an ice bath
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. customThe organics are separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customsubsequently evaporated to dryness in vacuo
  7. customThe crude product residue is then chromatographed by flash silica gel chromatography
  8. customevaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-f9578596aff347489f047a4b6e0f436c
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015220B2

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