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

HRID 1762843Notes

Reaction equation

HRID 1762843 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:5]=1)([O-])=O>C(O)C.C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:5]=1

Participants

5

Reactant 1

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

Product 1

HCID 200398344-[1-(4-Aminopyrid-2-yl)piperidin-4-yl]benzenesulphonamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of the product from part (i) (100 mg) and 5% palladium/carbon (25 mg) in ethanol (25 ml) and acetic acid (25 ml) was hydrogenated at 3.5 bars at room temperature for 3 hours. The catalyst was filtered off, the filtrate was evaporated and the residue was chromatographed on silica gel. Elution with dichloromethane/ethanol (19:1) gave some impurity and further elution with dichloromethane/ethanol/concentrated aqueous ammonia (90:10:1) gave the pure product. The combined product-containing fractions were evaporated to give the title compound as a monohydrate, m.p. 290°-295° (with decomp).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customthe residue was chromatographed on silica gel
  4. washElution with dichloromethane/ethanol (19:1)
  5. customgave
  6. washsome impurity and further elution with dichloromethane/ethanol/concentrated aqueous ammonia (90:10:1)
  7. customgave the pure product
  8. additionThe combined product-containing fractions
  9. customwere evaporated

Sources & evidence

ORD record
ord-0e4ce87d24934aa7915cd5828030fa25
Source dataset
uspto-grants-1989_05
Patent number
US04835165

Reaction notes

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