Sodium Carbonate → 3-[4-(6-Chloropyridazin-3-yl)piperazin-1-yl]propan-1-ol

HRID 80739Notes

Reaction equation

HRID 80739 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CC(N(C)C)=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:22]2[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][CH2:16][OH:15])[CH2:20][CH2:21]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 79207Piperazin-1-ylpropanol

Product 1

HCID 867627983-[4-(6-Chloropyridazin-3-yl)piperazin-1-yl]propan-1-olYield 50.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

3,6-dichloropyridazine (14.90 g, 100 mmol), sodium carbonate (10.60 g, 100 mmol) and DMA (80 mL) were placed in a 250 mL three-necked bottle, and the solution of 1-(3-hydroxypropyl)piperazine (14.4 g, 100 mmol) in DMA (20 mL) was added slowly in dropwise within 30 min under an ice-bath condition. The mixture was stirred at room temperature overnight, distilled under a reduced pressure to remove the solvent to obtain a brown solid, which was subjected to a column chromatography (gradient elution: petroleum/acetone system, v/v 2: 1 to acetone) to obtain a white solid, 13 g, yield 50.8%.

Workup

  1. distillationdistilled under a reduced pressure
  2. customto remove the solvent
  3. customto obtain a brown solid, which
  4. washwas subjected to a column chromatography (gradient elution: petroleum/acetone system, v/v 2: 1 to acetone)
  5. customto obtain a white solid, 13 g, yield 50.8%

Sources & evidence

ORD record
ord-bbf807ac7bde466092ec8dfe0bf284ae
Source dataset
uspto-grants-2014_09
Patent number
US08846678B2

Reaction notes

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