Acetyl chloride → 1-{3-[1-(3-Fluorophenyl)methylidene]piperidin-1-yl}ethanone

HRID 928078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928078
[C:1](Cl)(=[O:3])[CH3:2].Cl.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]2[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)[CH:10]=[CH:11][CH:12]=1.C(N(C(C)C)CC)(C)C>C1COCC1.O>[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:1](=[O:3])[CH3:2])[CH2:15]2)[CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 709838913-[1-(3-Fluorophenyl)methylidene]piperidine hydrochloride2×

Produkt 1

HCID 709845881-{3-[1-(3-Fluorophenyl)methylidene]piperidin-1-yl}ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Acetyl chloride (0.515 mL) was added to a mixture of 3-[1-(3-fluorophenyl)methylidene]-piperidine hydrochloride (Intermediate 226, 1.5 g) and N,N-di-isopropyl-N-ethylamine (2.52 mL) in anhydrous THF (50 mL) at 0° C. under nitrogen. The mixture was allowed to warm to room temperature and was stirred for 2 hours. The mixture was diluted with water (100 mL) and extracted with ether, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 75-100% to give 1-{3-[1-(3-fluorophenyl)-methylidene]piperidin-1-yl}ethanone (1.38 g).

Aufarbeitung

  1. extractionextracted with ether
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 75-100%

Quellen und Nachweise

ORD-Eintrag
ord-4354b4a830df48c2854eeaec51d107b0
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

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