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Potassium Carbonate → tert-Butyl 4-[4-(3-methoxy-3-oxopropyl)piperidin-1-yl]benzoate

HRID 446559
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 446559
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1.F[C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:12][O:11][C:9](=[O:10])[CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:14]2[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[CH:16][CH:15]=2)[CH2:2][CH2:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2736444Tert-butyl 4-fluorobenzoateHCID 10261546Methyl 3-(piperidin-4-yl)propanoate

Produkt 1

HCID 86663456tert-Butyl 4-[4-(3-methoxy-3-oxopropyl)piperidin-1-yl]benzoateAusbeute 32,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Methyl 3-(piperidin-4-yl)propanoate (WO2004/92124 A2) (206 mg, 1.11 mmol) was dissolved in N,N-dimethylformamide (10 mL), tert-butyl 4-fluorobenzoate (141 mg, 1.11 mmol) and potassium carbonate (100 mg, 1.11 mmol) were added, and the mixture was stirred at 120° C. under a nitrogen atmosphere for 16 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate, 10:1, v/v) to give the title compound (126 mg; yield, 31%) as a colorless oily substance.

Aufarbeitung

  1. customto separate the layers
  2. customThe resulting organic layer was separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (hexane

Quellen und Nachweise

ORD-Eintrag
ord-42346772ca714dc69f0744d71a88a445
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476253B2

Notizen zur Reaktion

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