1-(2-Hydroxyethyl)piperazine → 2-[4-(3,6-Dichloropyridazin-4-yl)-piperazin-1-yl]-ethanol

HRID 657594Notes

Reaction equation

HRID 657594 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1Cl.C(=O)([O-])[O-].[Na+].[Na+].[N:16]1([CH2:22][CH2:23][OH:24])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>CN(C)C(=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[N:19]1[CH2:20][CH2:21][N:16]([CH2:22][CH2:23][OH:24])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 10340Sodium CarbonateHCID 951233,4,6-Trichloropyridazine

Product 1

HCID 817655582-[4-(3,6-Dichloropyridazin-4-yl)-piperazin-1-yl]-ethanolYield 73.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In a 50 mL round bottom flask, 9.18 g (0.05 mol) of 3,4,6-trichloro-pyridazine, 5.30 g (0.05 mol) of anhydrous sodium carbonate and 20 mL of N,N-dimethylacetamide (DMA) were added, stirred at room temperature, then 6.54 g (0.05 mol) of 2-(piperazin-1-yl)-ethanol (dissolved in 10 ml DMA) was added dropwise slowly, stirred overnight, filtered on the next day. 100 mL of distilled water was added into the filter cake and stirred, then filtered again to obtain 10.20 g of a white solid, yield: 73.6%, m.p. 139˜141° C. 1H-NMR (400MHz, CDCl3) δppm: 2.57(br, 1H), 2.66˜2.68(t, 2H, J=5.12Hz), 2.73˜2.76(t, 4H, J=4.76Hz), 3.36˜3.38(t, 4H, J=4.52Hz), 3.68˜3.71(t, 2H, J=5.04Hz), 6.88(s, 1H). 13C-NMR (400MHz, DMSO-d6) δppm: 155.14, 149.43, 148.70, 116.64, 60.00, 58.49, 52.44, 48.90.

Workup

  1. stirringstirred overnight
  2. filtrationfiltered on the next day
  3. addition100 mL of distilled water was added into the filter cake
  4. stirringstirred
  5. filtrationfiltered again

Sources & evidence

ORD record
ord-bbc8d027ff8649cd99ce532d96180fd1
Source dataset
uspto-grants-2011_12
Patent number
US08076339B2

Reaction notes

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