Formaldehyde → 1,4-Bis[6-(3,4-dichlorophenyl)-3(2H)-pyridazinon-2-yl-methyl]piperazine

HRID 649130Notes

Reaction equation

HRID 649130 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12](=O)[NH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:16]=[O:17].[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[CH3:24][OH:25]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:24](=[O:25])[N:13]([CH2:12][N:18]3[CH2:23][CH2:22][N:21]([CH2:12][N:13]4[C:16](=[O:17])[CH:11]=[CH:10][C:9]([C:4]5[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=5)=[N:14]4)[CH2:20][CH2:19]3)[N:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 4837PiperazineHCID 6176896-(3,4-Dichlorophenyl)-3(2H)-pyridazinone

Product 1

HCID 132358781,4-Bis[6-(3,4-dichlorophenyl)-3(2H)-pyridazinon-2-yl-methyl]piperazineYield 88%

Procedure

To 40 ml of methanol were added 1.0 g of 6-(3,4-dichlorophenyl)-3(2H)-pyridazinone, 0.2 g of paraformaldehyde and 0.25 g of piperazine, and the resulting mixture was heated under reflux for 2 hours. The mixture was then left to cool, after which insolubles were collected by filtration and dried, to give 1.1 g (yield 88%) of the desired Compound No. 34, melting at 271°-272° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. waitThe mixture was then left
  4. temperatureto cool
  5. filtrationafter which insolubles were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-95fdc45f03dc44658e73702cf68d28e7
Source dataset
uspto-grants-1988_04
Patent number
US04738961

Reaction notes

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