4-Nitrobenzenesulfonyl chloride → HCID 21314857, compound

HRID 237022Notes

Reaction equation

N1C=CC=CC=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])C.[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([O-:22])=[O:21].O1CCC[CH2:34]1>>[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]2[C:18]2[CH:19]=[CH:34][CH:17]=[CH:16][N:15]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chloride

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 944591-(2-Pyridyl)piperazine

Product 1

HCID 21314857HCID 21314857, compoundYield 82%

Procedure

To a mixture of 6.42 g (0.03736 m) of 1-(2-pyridinyl)piperazine, 5.21 ml (0.03736 m) of triethylamine, and 250 ml of tetrahydrofuran is added 8.28 g (0.03736 m) of p-nitrobenzenesulfonyl chloride. The mixture is stirred at room temperature for 12/3 hours, after which it is concentrated in vacuo. The residue is then extracted with methylene chloride and aqueous sodium bicarbonate and the organic layer is taken to dryness to give 10.62 g (82%) of 1-[(p-nitrophenyl)sulfonyl]-(2-pyridinyl)piperazine.

Workup

concentrationafter which it is concentrated in vacuo
extractionThe residue is then extracted with methylene chloride and aqueous sodium bicarbonate

Sources & evidence

ORD record: ord-7dca74aaa92f4c2eb01bdb26ac029144
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159331

Reaction notes

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