Hydrochloric Acid → HCID 86629974, Verbindung

HRID 657636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657636
[H-].[Na+].[CH:3](OC)=[O:4].[CH3:7][C@H:8]1[CH2:13][C@H:12]([CH3:14])[CH2:11][N:10]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=2)[CH2:9]1.Cl>O1CCCC1>[CH3:14][C@H:12]1[CH2:13][C@H:8]([CH3:7])[CH2:9][N:10]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH2:26][CH:3]=[O:4])=[CH:21][CH:20]=2)[CH2:11]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 9795992HCID 9795992, Verbindung

Produkt 1

HCID 86629974HCID 86629974, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (82 mg, 60% in paraffin) are added methyl formate (150 μL) and a solution of trans-3,5-dimethyl-1-[3-(4-acetylphenoxy)propyl]piperidine (610 mg) in tetrahydrofuran (0.4 mL). The mixture is stirred for two hours at room temperature then hydrolysed with a 1N aqueous hydrochloric acid solution keeping the pH alkaline. The solution is extracted twice with ethyl acetate. The extracts are pooled, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with a gradient dichloromethane/methanol from 100/0 to 95/5. Fractions containing the expected product are pooled, concentrated under reduced pressure to give 100 mg of trans-3,5-dimethyl-1-{3-[4-(3-oxopropanoyl)phenoxy]propyl}piperidine as a pale yellow oil that is used rapidly, without further purification in the next step.

Aufarbeitung

  1. extractionThe solution is extracted twice with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by chromatography over silica gel with a gradient dichloromethane/methanol from 100/0 to 95/5
  5. additionFractions containing the expected product
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9b3feb5de2e74c9eaf06f8718d527bd3
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076329B2

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