1-(4-Nitrophenyl)piperazine → HCID 67106340, compound

HRID 1910819Notes

Reaction equation

HRID 1910819 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](Cl)(=[O:24])=[O:23])[CH:17]=1>N1C=CC=CC=1.C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([S:22]([C:18]3[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=3)(=[O:24])=[O:23])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 804471-(4-Nitrophenyl)piperazineHCID 3164136Pyridine-3-sulfonyl chloride

Product 1

HCID 67106340HCID 67106340, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-nitrophenyl)-piperazine (2.50 g, 12.1 mmol) in pyridine (15 mL) was added a solution of pyridine-3-sulfonyl chloride (2.78 g, 15.7 mmol) in THF (30 mL) under an argon atmosphere at 0° C. The reaction was warmed to r.t. and stirred for 2 h, before the mixture was evaporated to dryness. The residue was partitioned between water and dichloromethane, the organic layer separated and washed successively with sat. sodium bicarbonate solution, water and brine. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was subjected to column chromatography over neutral alumina using 5% to 70% ethyl acetate in petroleum ether as eluent to afford 1-(4-nitrophenyl)-4-(pyridine-3-sulfonyl)-piperazine (1.63 g, 39%) as a yellow solid.

Workup

  1. customwas evaporated to dryness
  2. customThe residue was partitioned between water and dichloromethane
  3. customthe organic layer separated
  4. washwashed successively with sat. sodium bicarbonate solution, water and brine
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3cf5a73760c4cbdaaaf5e2246f9cfb4
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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