Sodium Bicarbonate → N-[4-([1-(4-nitro-2-pyridyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamide

HRID 345449Notes

Reaction equation

HRID 345449 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.Cl[C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][N:22]=1.C(=O)(O)[O-].[Na+]>C(O)CCC>[N+:27]([C:25]1[CH:24]=[CH:23][N:22]=[C:21]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=3)[CH2:3][CH2:2]2)[CH:26]=1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7351522-Chloro-4-nitropyridineHCID 19992428N-[4-([Piperidin-4-yl]methoxy)phenyl]methanesulphonamide

Product 1

HCID 19992415N-[4-([1-(4-nitro-2-pyridyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of the product of part (v) (0.50 g), 2-chloro-4-nitropyridine (0.28 g) and sodium bicarbonate (1.00 g) in n-butanol (20 ml) was heated under reflux with stirring for 18 hours. The mixture was cooled, filtered, and the residue was washed with ethanol. The combined filtrate and washings were evaporated to give a gum which was chromatographed on silica gel eluting with ether. Earlier fractions gave impurity and the pure product was eluted in the later fractions. The product fractions were combined and evaporated to give the product, (0.21 g), m.p. 183.5°-184.5° (from ethanol).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe residue was washed with ethanol
  6. customThe combined filtrate and washings were evaporated
  7. customto give a gum which
  8. customwas chromatographed on silica gel eluting with ether
  9. customEarlier fractions gave impurity
  10. washthe pure product was eluted in the later fractions
  11. customevaporated
  12. customto give the product, (0.21 g), m.p. 183.5°-184.5° (from ethanol)

Sources & evidence

ORD record
ord-208b390797d24e6fb9e6433422cbd5d8
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

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