Dimethylformamide → 4-(Piperidin-1-yl)benzaldehyde

HRID 992461

Reaktionsgleichung

Reaktionsgleichung von HRID 992461
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[C:11]1([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCCl>[N:17]1([C:11]2[CH:16]=[CH:15][C:14]([CH:3]=[O:4])=[CH:13][CH:12]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 200381-PhenylpiperidineHCID 24813Phosphorus oxychloride

Produkt 1

HCID 2913544-(Piperidin-1-yl)benzaldehydeAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 2.3 mL (30 mmoles) of N,N-dimethylformamide in 10 mL of 1,2-dichloroethane was added dropwise 2.8 mL (30 mmoles) of phosphorus oxychloride at 0° C. The ice-bath was removed and the reaction mixture was stirred for 15 min. 1-Phenylpiperidine (3.2 mL, 20 mmoles) was added to the above solution portionwise and the reaction mixture was refluxed overnight. The reaction mixture was poured into ice-cold 2N sodium hydroxide solution and stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with 2×20 mL of ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was separated on a silica gel column eluting with ethyl acetate and hexane to afford 1.5 g (40%) of the title compound as a white solid.

Aufarbeitung

  1. customThe ice-bath was removed
  2. temperaturethe reaction mixture was refluxed overnight
  3. stirringstirred at room temperature for 1 h
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with 2×20 mL of ethyl acetate
  6. washThe combined organic layer was washed with brine until pH=7
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customThe residue was separated on a silica gel column
  10. washeluting with ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-1187132d7d8e4969b98cac9f9b62b9cb
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06469032B2

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