Dichloromethane → HCID 67067092, compound

HRID 2074262Notes

Reaction equation

HRID 2074262 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl.Cl.Cl.[N:16]1([C:22]([O:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C(Cl)(Cl)Cl>[C:1]1([S:7]([N:19]2[CH2:20][CH2:21][N:16]([C:22]([O:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[O:23])[CH2:17][CH2:18]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 67067109HCID 67067109, compound

Product 1

HCID 67067092HCID 67067092, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

TEA (0.23 ml) and benzenesulfonyl chloride (0.075 ml) were added to a dichloromethane (5 ml) solution containing 3-pyridyl 1-piperazinecarboxylate dihydrochloride (150 mg), followed by stirring overnight at room temperature. The reaction solution was diluted with chloroform, the organic layer was washed with aqueous saturated sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (eluent: chloroform), and the resulting solid was recrystallized from 2-propanol to obtain 3-pyridyl 4-(phenylsulfonyl)-1-piperazinecarboxylate (130 mg).

Workup

  1. washthe organic layer was washed with aqueous saturated sodium hydrogencarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: chloroform)
  5. customthe resulting solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-5860ddb59f0d42b4a172a25a36e01137
Source dataset
uspto-grants-2011_04
Patent number
US07919494B2

Reaction notes

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