2-Phenylpropionic acid → 1-(4-Hydroxypiperidin-1-yl)-3-phenylpropan-1-one

HRID 584720

Reaktionsgleichung

Reaktionsgleichung von HRID 584720
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]1([CH2:14][CH2:15][C:16](Cl)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C(C)C(O)=O)C=CC=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:8]1([CH2:14][CH2:15][C:16]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 102962-Phenylpropionic acidHCID 14798Sodium HydroxideHCID 64801Benzenepropanoyl chlorideHCID 79341Piperidin-4-ol

Produkt 1

HCID 221751621-(4-Hydroxypiperidin-1-yl)-3-phenylpropan-1-oneAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

This amine was synthesized in accordance with the method of Scheme 37. To 4 g (40 mmol) of 4-hydroxypiperidine in 20 mL of toluene was added phenylpropionyl chloride (derived from 6 g (40 mmol) of phenylpropionic acid in excess thionyl chloride). To the mixture was added excess 2N aqueous NaOH. After stirring 24 hours, the toluene layer was discarded and the aqueous phase was extracted with CH2Cl2, dried, and evaporated under vacuum to give 3.63 g (39%) of 1-(3-phenylpropionyl)-4-hydroxypiperidine (134). GC/MS indicated 100% purity with a molecular ion of 233.

Aufarbeitung

  1. extractionthe aqueous phase was extracted with CH2Cl2
  2. customdried
  3. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4aaa411c929e403e9ecc69ab41cbaa19
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927225B2

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