2-Chloro-4-nitropyridine → 4-[1-(4-Nitropyrid-2-yl)piperidin-4-yl]benzenesulphonamide

HRID 1762842Notes

Reaction equation

HRID 1762842 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][N:19]=1>N1C=CC=CC=1>[N+:24]([C:22]1[CH:21]=[CH:20][N:19]=[C:18]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]3[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:14])=[O:15])=[CH:9][CH:8]=3)[CH2:3][CH2:2]2)[CH:23]=1)([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 7351522-Chloro-4-nitropyridineHCID 183484304-Piperidin-4-YL-benzenesulfonamide

Product 1

HCID 200398354-[1-(4-Nitropyrid-2-yl)piperidin-4-yl]benzenesulphonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-(4-piperidinyl)benzensulphonamide [the product of Example 2(iii)] (0.46 g) and 2-chloro-4-nitropyridine (0.30 g) in pyridine (10 ml) was heated under reflux for 5 hours and then evaporated. The residue was partitioned between dichloromethane and 10% aqueous sodium carbonate solution. The aqueous layer was extracted several times with dichloromethane nd the combined organic extracts were dried (MgSO4) and evaporated. The residue was chromatographed on silica gel. Elution with dichloromethane/methanol (99:1) first gave impurity followed by the pure product. The product-containing fractions were combined and evaporated to give the title compound, (0.15 g), m.p. 215°-217°.

Workup

  1. temperatureunder reflux for 5 hours
  2. customevaporated
  3. customThe residue was partitioned between dichloromethane and 10% aqueous sodium carbonate solution
  4. extractionThe aqueous layer was extracted several times with dichloromethane
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washElution with dichloromethane/methanol (99:1) first gave impurity
  9. customevaporated

Sources & evidence

ORD record
ord-93185f50042d43eb8e34b9f9fdef74ee
Source dataset
uspto-grants-1989_05
Patent number
US04835165

Reaction notes

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