4-Hydroxybenzaldehyde → HCID 18663243, Verbindung

HRID 1956455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1956455
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16]I)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>C(OCC)(=O)C>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 9975355Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylate

Produkt 1

HCID 18663243HCID 18663243, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-(N-Boc-piperidin-4-yl)propyl iodide 1-1 (5.0 g, 14.2 mmol) (preparation described in EP 478,328), 4-hydroxybenzaldehyde 1-2 (1.73 g, 14.2 mmol), Cs2CO3 (9.2 g, 28.4 mmol) and DMF (50 ml) was stirred at ambient temperature for 2.0 hours. The reaction mixture was diluted with ethyl acetate and then washed with H2O, sat. NaHCO3, 10% KHSO4, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 10% EtOAc/hexane) provided 1-3 as a white solid.

Aufarbeitung

  1. washwashed with H2O, sat. NaHCO3, 10% KHSO4, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6768061557b7413a87d4bae93df62a2e
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780480

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