Piperazine → 1-[4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazine

HRID 582302Notes

Reaction equation

HRID 582302 reaction equation
[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)=[O:18])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>C(Cl)Cl>[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:23]([N:42]4[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]4)=[O:24])=[CH:26][CH:27]=3)=[O:18])[CH2:15][CH2:16]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 4837PiperazineHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 109595584-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid

Product 1

HCID 540321271-[4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoyl]piperazineYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid (1.5 g) was dissolved in methylene chloride (50 ml) and then, triethylamine (0.7 ml) was added and cooled. Pivaloyl chloride (0.58 ml) was added slowly to the solution at 0~5° C. and the mixture was stirred at 5° C. for 2 hours. With the addition of piperazine (0.9 g), the solution was stirred at 5~10° C. for 3 hours. The reaction mixture was washed with water and aqueous sodium bicarbonate and the solvent was concentrated under reduced pressure. The concentrated residue was crystallized by treatment with ether and further recrystallized using isopropanol and ether. The recrystallized product was filtered and dried to give 1.48 g (yield: 83%) of the desired compound as white crystal.

Workup

  1. temperaturecooled
  2. stirringthe solution was stirred at 5~10° C. for 3 hours
  3. washThe reaction mixture was washed with water and aqueous sodium bicarbonate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe concentrated residue was crystallized by treatment with ether
  6. customfurther recrystallized
  7. filtrationThe recrystallized product was filtered
  8. customdried

Sources & evidence

ORD record
ord-9cdda9355f3e4516836bc4ea8ef49b16
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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