4-Hydroxybenzaldehyde → 4-(1-Acetylpiperidin-4-yloxy)benzaldehyde

HRID 591710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591710
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:10])[CH3:9])[CH2:4][CH2:3]1.O[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:8]([N:5]1[CH2:6][CH2:7][CH:2]([O:1][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)[CH2:3][CH2:4]1)(=[O:10])[CH3:9]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

Produkt 1

HCID 230875244-(1-Acetylpiperidin-4-yloxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-hydroxy-piperidin-1-yl)-ethanone (1.00 g, 6.90 mmol), 4-hydroxybenzaldehyde (0.854 g, 6.90 mmol) and triphenylphosphine (1.83 g, 6.90 mmol) in THF (10 mL) was added dropwise diisopropyl azodicarboxylate (DIAD) (1.41 g, 6.90 mmol). The reaction mixture was stirred at room temperature for 16 hours, THF was evaporated, and the residue was purified by column chromatography, using dichloromethane:ethyl acetate:methanol (1:2:0.05) as eluent, to give 4-(1-acetyl-piperidin-4-yloxy)-benzaldehyde. Yield: 0.40 g (23%).

Aufarbeitung

  1. customTHF was evaporated
  2. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-965e33a22ff849faace415dd0cc2be03
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238640B2

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