Ammonium Chloride → 4-(Hydroxymethyl)-1-phenylpiperidin-2-one

HRID 341050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341050
[O:1]=[C:2]1[CH2:7][CH:6]([C:8](OCC)=[O:9])[CH2:5][CH2:4][N:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>O1CCCC1>[OH:9][CH2:8][CH:6]1[CH2:5][CH2:4][N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:2](=[O:1])[CH2:7]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 53699167Ethyl 2-oxo-1-phenylpiperidine-4-carboxylate

Produkt 1

HCID 154282234-(Hydroxymethyl)-1-phenylpiperidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Ethyl 2-oxo-1-phenylpiperidine-4-carboxylate (0.31 g, 1.3 mmol) was dissolved in tetrahydrofuran (10 mL), cooled to −78° C. and treated with lithium aluminum hydride (0.16 mL, 2 M tetrahydrofuran solution, 3.8 mmol, 3 equiv). The mixture was warmed to −40° C., stirred for 1 hour and treated with ammonium chloride (50 mL, aqueous saturated). The aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Aufarbeitung

  1. temperatureThe mixture was warmed to −40° C.
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. dry with materialthe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7ef7db432585403cb2e79448f602ade4
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895580B2

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