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

HRID 344665Notes

Reaction equation

HRID 344665 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 103222122-[4-(2,3,4-Trimethoxybenzyl)-1-piperazinyl]-5-n-propylbenzenesulfonic acidYield 59.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f712bf46adec498eb2049a7584260849
Source dataset
uspto-grants-1991_10
Patent number
US05053409

Reaction notes

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