2,3,4-Trimethoxybenzaldehyde → 2-[4-(2,3,4-Trimethoxybenzyl)-1-piperazinyl]-5-n-propylbenzenesulfonic acid

HRID 344665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 344665
C([BH3-])#N.[Na+].[N:5]1([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH3:19])=[CH:13][C:12]=2[S:20]([OH:23])(=[O:22])=[O:21])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH3:24][O:25][C:26]1[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=[CH:30][C:27]=1[CH:28]=O>CO.[Cl-].[Zn+2].[Cl-]>[CH3:24][O:25][C:26]1[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=[CH:30][C:27]=1[CH2:28][N:8]1[CH2:9][CH2:10][N:5]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH3:19])=[CH:13][C:12]=2[S:20]([OH:23])(=[O:21])=[O:22])[CH2:6][CH2:7]1

Komponenten

6

Edukt 3

HCID 750062,3,4-TrimethoxybenzaldehydeHCID 30273132-(1-Piperazinyl)-5-n-propylbenzenesulfonic acidHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 103222122-[4-(2,3,4-Trimethoxybenzyl)-1-piperazinyl]-5-n-propylbenzenesulfonic acidAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Into a solution of 0.10 g of sodium cyanoborohydride dissolved in 2 ml of a methanol solution was added 0.10 g of zinc chloride, and the mixture was stirred for 5 minutes. Then, 0.40 g of 2-(1-piperazinyl)-5-n-propylbenzenesulfonic acid and 0.58 g of 2,3,4-trimethoxybenzaldehyde were added to carry out the reaction at room temperature for 2 hours. The organic layer was extracted by addition of an aqueous sodium chloride and tetrahydrofuran, and after evaporation of tetrahydrofuran under reduced pressure from the extract, the residue was purified by silicagel column chromatography (eluant:chloroform: methanol:acetic acid=500:100:6) to give 0.39 g (yield: 58.5%) of the above title product as a glassy solid.

Aufarbeitung

  1. customthe reaction at room temperature for 2 hours
  2. extractionThe organic layer was extracted by addition of an aqueous sodium chloride and tetrahydrofuran
  3. customafter evaporation of tetrahydrofuran under reduced pressure from the extract
  4. customthe residue was purified by silicagel column chromatography (eluant:chloroform: methanol:acetic acid=500:100:6)

Quellen und Nachweise

ORD-Eintrag
ord-f712bf46adec498eb2049a7584260849
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053409

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