Pyridine → 1-[(4-Chloro-3-nitrophenyl)sulfonyl]-4-methylpiperazine

HRID 241417Notes

Reaction equation

HRID 241417 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].N1C=CC=CC=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 531671-Methylpiperazine

Product 1

HCID 28424191-[(4-Chloro-3-nitrophenyl)sulfonyl]-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.1 2.5 g (9.763 mmol) of 4-chloro-3-nitrobenzenesulfonyl chloride are dissolved in 100 ml of DCM. 1.574 ml (19.5 mmol) of pyridine and 1.086 ml (9.760 mmol) of N-methylpiperazine are added, and the mixture is stirred at room temperature for 14 h. The reaction mixture is washed 3× with water, the organic phase is dried using sodium sulfate, filtered, and the solvent is removed, giving 1-(4-chloro-3-nitrobenzenesulfonyl)-4-methylpiperazine; EI-MS [M]+ 319.

Workup

  1. washThe reaction mixture is washed 3× with water
  2. customthe organic phase is dried
  3. filtrationfiltered
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-5fd684ef0afc46b79e31ca699ba51326
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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