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

HRID 1797036

Reaktionsgleichung

Reaktionsgleichung von HRID 1797036
[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-6bbe7f7bc04640a7a2e7ea520760f651
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034035B2

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