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Hydrochloric Acid → 1-[(1S)-1-(2-Naphthalenyl)ethyl]-4-piperidinone

HRID 897225
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 897225
COC(=O)[CH2:4][CH2:5][N:6]([CH2:19][CH2:20][C:21]([O:23]C)=O)[C@H:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[CH3:8].[H-].[Na+].Cl.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC(O)=O>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[C@@H:7]([N:6]1[CH2:19][CH2:20][C:21](=[O:23])[CH2:4][CH2:5]1)[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 69697317HCID 69697317, Verbindung

Produkt 1

HCID 697035741-[(1S)-1-(2-Naphthalenyl)ethyl]-4-piperidinoneAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (S)-methyl-3-[(2-methoxycarbonylethyl)-(1-naphthalen-2-yl-ethyl)-amino]-propanoate (3.6 g, 10 mmol) in toluene (20 mL), NaH (0.5 g, 13 mmol) was added and the mixture was refluxed in an oil bath kept at 150° C. for 6 hours. After cool, the reaction mixture was acidified with AcOH and extracted with benzene. The organic layer was dried over MgSO4, and concentrated to afford a crude oil. The oil was boiled with 10% HCl (20 mL) for 18 hours. The aqueous solution was basified with K2CO3 and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated. The crude oil was purified by chromatography on silica gel with ethyl acetate/hexanes (1:4) to give the title compound (1.2 g, 47%). 1H NMR (300 MHz, CDCl3) δ 1.51 (3H, d, J=6.59 Hz), 2.44 (4H, t, J=6.03 Hz), 2.71-2.90 (4H, m), 3.79 (1H, q, J=6.78 Hz), 7.42-7.60 (3H, m), 7.72-7.86 (4H, m).

Aufarbeitung

  1. temperaturethe mixture was refluxed in an oil bath
  2. temperatureAfter cool
  3. extractionextracted with benzene
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customto afford a crude oil
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over MgSO4
  9. customevaporated
  10. customThe crude oil was purified by chromatography on silica gel with ethyl acetate/hexanes (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-beff979d26fb42cdb32b555b234122e8
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06921821B2

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