Diisopropylethylamine → 2-Fluoro-6-(4-methanesulfonylpiperidine-1-yl)benzaldehyde

HRID 41968

Reaktionsgleichung

Reaktionsgleichung von HRID 41968
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].Cl.[CH3:12][S:13]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])=[O:14].CCN(C(C)C)C(C)C>C(#N)C>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([N:19]2[CH2:20][CH2:21][CH:16]([S:13]([CH3:12])(=[O:15])=[O:14])[CH2:17][CH2:18]2)[C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1362842,6-DifluorobenzaldehydeHCID 230616984-Methanesulfonylpiperidine hydrochloride

Produkt 1

HCID 581379622-Fluoro-6-(4-methanesulfonylpiperidine-1-yl)benzaldehydeAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a 250 mL round bottom flask, 2,6-difluorobenzaldehyde (7.12 g, 5.4 mL, 50.1 mmol), 4-methanesulfonylpiperidine hydrochloride (10 g, 50.1 mmol) and DIPEA (7.77 g, 60.1 mmol) were combined with acetonitrile (75 mL). The mixture was stirred and heated at 80° C. overnight. The mixture was evaporated and extracted with dichloromethane and citric acid solution. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The crude solid was triturated with cold ethyl acetate to afford 2-fluoro-6-(4-methanesulfonylpiperidine-1-yl)benzaldehyde (12 g, 84% yield). LC-MS calcd for C13H16FNO3S (m/e) 285.08, obsd 286.0 (M+H).

Aufarbeitung

  1. customThe mixture was evaporated
  2. extractionextracted with dichloromethane and citric acid solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude solid was triturated with cold ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7604022984de470db2eaaeb7e6b15206
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536172B2

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