Thiophene → 3-Chloro-6-[4-(2-phenylethyl)-1-piperazinyl]pyridazine

HRID 466572Notes

Reaction equation

HRID 466572 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1.S1[CH:18]=[CH:17][CH:16]=[CH:15]1.[H][H]>CO.[Pt]>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:2][CH:7]=[CH:6][CH:5]=3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 52949263-Chloro-6-(1-piperazinyl)pyridazineHCID 178418361HCID 178418361, compound

Product 1

HCID 151246153-Chloro-6-[4-(2-phenylethyl)-1-piperazinyl]pyridazineYield 33%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 3 parts of 3-chloro-6-(1-piperazinyl)pyridazine, 2 parts of benzeneacetylaldehyde, 1 part of a solution of thiophene in methanol 4% and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 1.5 parts (33%) of 3-chloro-6-[4-(2-phenylethyl)-1-piperazinyl]pyridazine; mp. 140.0° C. (compound 231).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from 2-propanol
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-3b9d7bae08e74954b78f87a66181ec1e
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

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