2-Phenylpiperidine → 3-Chloro-4-hydroxybenzoic Acid {2-Methoxy-4-[2-(2-phenylpiperidin-1-yl)ethoxy]benzylidene}hydrazide

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][NH2:8])=[O:6].Br[CH2:14][CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[C:19]([O:25][CH3:26])[CH:18]=1.[C:27]1([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][NH:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([O:16][CH2:15][CH2:14][N:34]2[CH2:35][CH2:36][CH2:37][CH2:38][CH:33]2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:20]=1[CH:21]=[N:8][NH:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=1

Komponenten

Edukt 3

HCID 1030202-Phenylpiperidine

HCID 109542683-Chloro-4-hydroxybenzohydrazide

HCID 229991114-(2-Bromoethoxy)-2-methoxybenzaldehyde

Produkt 1

HCID 725141593-Chloro-4-hydroxybenzoic Acid {2-Methoxy-4-[2-(2-phenylpiperidin-1-yl)ethoxy]benzylidene}hydrazide

Versuchsvorschrift

This compound was prepared analogously to the compound described in the previous example starting from resin bound 3-chloro-4-hydroxybenzoic acid hydrazide (resin—[building block 1]) (2 g, ˜2 mmoles), 4-(2-bromoethoxy)-2-methoxybenzaldehyde ([building block 2]) (0.73 g, 1.5 equivs.), and 2-phenylpiperidine ([building block 3]) (3.0 g, 10 equivs.). After cleavage with 50% trifluoroacetic acid, the residue (1.0 g) was purified by column chromatography on silica gel (28 g) eluting with a mixture of methanol and dichloromethane (1:13). This afforded 0.24 g of the title compound.