Thiophene → HCID 86744609, compound

HRID 1030934Notes

Reaction equation

HRID 1030934 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.[CH:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)=O.S1C=CC=C1.[H][H]>[Pt].CO.C(N(CC)CC)C>[ClH:1].[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8030ThiopheneHCID 120884-Formylbenzoic acidHCID 52949263-Chloro-6-(1-piperazinyl)pyridazineHCID 178418361HCID 178418361, compound

Product 1

HCID 86744609HCID 86744609, compoundYield 35.2%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2 parts of 3-chloro-6-(1-piperazinyl)pyridazine, 2 parts of 4-formylbenzoic acid, 2 parts of a thiophene solution 4%, 1.5 parts of N,N-diethylethanamine and 80 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 filterate was evaporated. The residue was converted into the hydrochoride salt in 2-propanol. The precipitated product was filtered off, washed with 2-propanol and 2,2'-oxybispropane and dried at 50° C., yielding 1.3 parts (35.2%) of 4-[[4-(6-chloro-3-pyridazinyl)-1-piperazinyl]methyl]benzoic acid monohydrochloride; mp.>300° C. (comp. 98).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filterate was evaporated
  3. filtrationThe precipitated product was filtered off
  4. washwashed with 2-propanol and 2,2'-oxybispropane
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-c151f0d3d997426c9c2f3342daaaf405
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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