Potassium Hydroxide → 1-(4-Methoxy-benzyl)-3-propyl-piperidine

HRID 492647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492647
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=O)[CH2:15][CH3:16])[CH2:9]2)=[CH:5][CH:4]=1.[OH-].[K+].O.NN.[NH4+].[Cl-]>C(O)COCCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][CH3:16])[CH2:9]2)=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 25517Ammonium ChlorideHCID 597303451-[1-(4-Methoxy-benzyl)-piperidin-3-yl]-propan-1-one

Produkt 1

HCID 597300471-(4-Methoxy-benzyl)-3-propyl-piperidineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8117Diethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Combine 1-[1-(4-Methoxy-benzyl)-piperidin-3-yl]-propan-1-one (277.3 mg, 1.07 mmol), Diethylene glycol (10 mL), KOH (178.0 mg, 3.18 mmol), and Hydrazine-monohydrate (1.0 mL) at room temperature under a Nitrogen atmosphere. Heat the reaction mixture to 120° C. for 2 hours and then 220° C. for 4 hours. Cool reaction to room temperature and then pour the reaction mixture over sat NH4Cl (aq). Extract with Ethyl acetate, wash with brine, and dry over Na2SO4. Concentrate under reduced pressure and flash chromatograph using 3% 1N NH3 MeOH in CH2Cl2 to give 105.2 mg (40% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 0.9 (3H, t), 1.1-1.4 (4H, m), 1.5-1.7 (3H, m), 1.7 (1H, d), 1.9 (1H, td), 2.7-2.9 (2H, m), 3.5 (2H, dd), 3.8 (3H, s), 6.8 (2H, d), 7.2 (2H, d); MS m/z 248 (M+1).

Aufarbeitung

  1. customat room temperature
  2. temperatureCool
  3. customreaction to room temperature
  4. additionpour the reaction mixture
  5. extractionExtract with Ethyl acetate
  6. washwash with brine
  7. dry with materialdry over Na2SO4
  8. concentrationConcentrate under reduced pressure and flash chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-d777ed9e91214ac6bc46a320cab7d7fa
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531557B2

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