1-(4-Pyridyl)piperazine → 1-[4-(4-(3-Chlorophenyl)piperazin-1-ylsulphonyl)benzoyl]-4-(4-pyridyl)piperazine

HRID 346679

Reaction equation

HRID 346679 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.Cl.[Cl:16][C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1.[N:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[CH:31][CH:30]=1>C(N(CC)CC)C.ClCCl>[Cl:16][C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][N:26]([S:2]([C:5]3[CH:6]=[CH:7][C:8]([C:9]([N:38]4[CH2:39][CH2:40][N:35]([C:32]5[CH:33]=[CH:34][N:29]=[CH:30][CH:31]=5)[CH2:36][CH2:37]4)=[O:11])=[CH:12][CH:13]=3)(=[O:3])=[O:4])[CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 705171-(4-Pyridyl)piperazineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 119574871-(3-Chlorophenyl)piperazine dihydrochloride

Product 1

HCID 179157301-[4-(4-(3-Chlorophenyl)piperazin-1-ylsulphonyl)benzoyl]-4-(4-pyridyl)piperazineYield 17.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-(Chlorosulphonyl)benzoic acid (0.75 g) was added to a solution of 1-(3-chlorophenyl)piperazine dihydrochloride (0.90 g) in triethylamine (2.4 ml) and dichloromethane (50 ml). The reaction mixture was stirred overnight at room temperature then concentrated in vacuo. The resulting solid was suspended in N,N-dimethylformamide (50 ml) and carbonyl diimidazole (0.55 g) was added. The reaction mixture was stirred for one hour at room temperature then 1-(4-pyridyl)piperazine (0.55 g, 3.4 mmol) was added. The reaction mixture was stirred for three hours, then concentrated in vacuo. The resulting solid was separated between ethyl acetate (100 ml) and water (100 ml). The ethyl acetate layer was washed with aqueous saturated sodium bicarbonate solution (100 ml) then dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting yellow oil was subjected to chromatography (SiO2: 10%-12% MeOH/EtOAc) to yield 1-[4-(4-(3-chlorophenyl)piperazin-1-ylsulphonyl)benzoyl]-4-(4-pyridyl)piperazine as a white solid (300.1 mg);

Workup

  1. concentrationthen concentrated in vacuo
  2. additioncarbonyl diimidazole (0.55 g) was added
  3. stirringThe reaction mixture was stirred for one hour at room temperature
  4. stirringThe reaction mixture was stirred for three hours
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was separated between ethyl acetate (100 ml) and water (100 ml)
  7. washThe ethyl acetate layer was washed with aqueous saturated sodium bicarbonate solution (100 ml)
  8. dry with materialthen dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84252e9f96f54004a50597c728b5d962
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Linked notes

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