Sodium Carbonate → 3-Bromo-6-[4-(3-methylphenyl)-1-piperazinyl]pyridazine

HRID 466557Notes

Reaction equation

HRID 466557 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:22][C:23]1[N:24]=[N:25][C:26](Br)=[CH:27][CH:28]=1>CN(C)C=O>[Br:22][C:23]1[N:24]=[N:25][C:26]([N:13]2[CH2:14][CH2:15][N:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH3:3])[CH:5]=3)[CH2:11][CH2:12]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 831101-(m-Tolyl)piperazine dihydrochlorideHCID 2488523,6-Dibromopyridazine

Product 1

HCID 5033263-Bromo-6-[4-(3-methylphenyl)-1-piperazinyl]pyridazineYield 61.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 5 parts of 1-(3-methylphenyl)piperazine dihydrochloride, 10.6 parts of sodium carbonate and 180 parts of N,N-dimethylformamide was stirred for 1 hour at 65° C. Then there were added 7.2 parts of 3,6-dibromopyridazine and the whole was stirred overnight at about 65° C. The reaction mixture was poured into ice water. The product was filtered off and dissolved in dichloromethane. The solution was washed twice with water, dried, filtered and evaporated. The residue was crystallized from ethanol. The product was filtered off and dried, yielding 4.1 parts (61.5%) of 3-bromo-6-[4-(3-methylphenyl)-1-piperazinyl]pyridazine; mp. 145.7° C. (compound 136).

Workup

  1. stirringthe whole was stirred overnight at about 65° C
  2. filtrationThe product was filtered off
  3. dissolutiondissolved in dichloromethane
  4. washThe solution was washed twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from ethanol
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-4138cb209a69424abe1aa1f8b81038e0
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

Loading…