2-(4-Fluorophenyl)oxirane → 1-[2-Hydroxy-2-(4-fluorophenyl)ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine

HRID 497353

Reaktionsgleichung

Reaktionsgleichung von HRID 497353
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(O)C>[OH:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:10][N:30]1[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][CH2:24][CH2:23][C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:21]=[CH:22][C:13]=2[O:12][CH3:11])[CH2:32][CH2:31]1

Komponenten

4

Edukt 2

HCID 40652302-(4-Fluorophenyl)oxiraneHCID 223186531-[4-(2-Methoxynaphthalen-1-yl)butyl]piperazine

Produkt 1

HCID 223186441-[2-Hydroxy-2-(4-fluorophenyl)ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

0.80 g of the optically active form of 2-(4-fluorophenyl)oxirane was dissolved in ethanol, and 3.2 g of 1-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine was added, followed by reflux with heating or 2 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in chloroform and washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=2:1) to give 1.2 g of optically active 1-[2-hydroxy-2-(4-fluorophenyl)ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin as a solid.

Aufarbeitung

  1. temperatureby reflux
  2. temperaturewith heating or 2 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with a saturated aqueous sodium bicarbonate solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customAfter removal of the drying agent
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e965505911144bbd8466f4ae43d923ea
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949552B2

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