Potassium Carbonate → 3,6-Dichloro-4-((4-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)amino)pyridazine

HRID 1087158Notes

Reaction equation

HRID 1087158 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1Cl.C(=O)([O-])[O-].[K+].[K+].[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:23][CH2:22]1>C(#N)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 951233,4,6-TrichloropyridazineHCID 109999031-(4-Aminobutyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 147264603,6-Dichloro-4-((4-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)amino)pyridazineYield 54.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9.25 g (0.050 mol) of 3,4,6-trichloropyridazine are stirred with 6.90 g (0.050 mol) of powdered anhydrous potassium carbonate and 13.15 g (0.050 mol) of 1-(4-aminobutyl)-4-(2-methoxyphenyl)piperazine in 1350 ml of dry acetonitrile at room temperature for 96 hours. The mixture is subsequently filtered with suction, and the filtrate is concentrated in vacuo. The residue is taken up in ethanol, and the trihydrochloride of 3,6-dichloro-4-((4-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)amino)pyridazine of m.p.: 155°-170° C. is precipitated with ethereal HCl; yield: 54.2% of theory.

Workup

  1. filtrationThe mixture is subsequently filtered with suction
  2. concentrationthe filtrate is concentrated in vacuo
  3. customthe trihydrochloride of 3,6-dichloro-4-((4-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)amino)pyridazine of m.p.: 155°-170° C. is precipitated with ethereal HCl

Sources & evidence

ORD record
ord-e2ecf7f680624a02b4740b552ea00331
Source dataset
uspto-grants-1991_07
Patent number
US05034391

Reaction notes

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