Potassium Hydroxide → 3-Butyl-1-(4-methoxy-benzyl)-piperidine

HRID 131049

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=O)[CH2:15][CH2:16][CH3:17])[CH2:9]2)=[CH:5][CH:4]=1.[OH-].[K+].O.NN.[NH4+].[Cl-]>C(O)COCCO>[CH2:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:9]1)[CH2:15][CH2:16][CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

Combine 1-[1-(4-Methoxy-benzyl)-piperidin-3-yl]-butan-1-one (356.0 mg, 0.95 mmol), Diethylene glycol (15 mL), KOH (479.0 mg, 8.54 mmol), and Hydrazine-monohydrate (1.8 mL) at room temperature under a Nitrogen atmosphere. Heat the reaction mixture to 120° C. for 2 hours and then 220° C. for 24 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 NH3MeOH in CH2Cl2 to give 220.7 mg (89% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 0.7-0.9 (3H, m), 1.1-1.4 (4H, m), 1.5-1.7 (4H, m), 1.7 (1H, d), 1.9 (1H, t), 2.8 (2H, t), 3.4 (2H, dd), 3.6-3.7 (3H, m), 3.8 (3H, s), 6.8 (2H, d), 7.2 (2H, d); MS m/z 262 (M+1).

Aufarbeitung

customat room temperature
temperatureCool
customreaction to room temperature
additionpour the reaction mixture
extractionExtract with Ethyl acetate
washwash with brine
dry with materialdry over Na2SO4
concentrationConcentrate under reduced pressure and flash chromatograph

Quellen und Nachweise

ORD-Eintrag: ord-6e0803076ca548148366ebe5a232277d
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07381719B2

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