Hydrochloric Acid → N-{1-[2-(6-Methyl-2-pyridyl)ethyl]-4-piperidyl}-4-(N-methylamino)benzenesulfonamide

HRID 1377024

Reaction equation

HRID 1377024 reaction equation
C(O)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([C:23](=O)C)C)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:7][CH2:6]1.[CH3:26][C:27]1[N:32]=[C:31]([CH:33]=[CH2:34])[CH:30]=[CH:29][CH:28]=1.C([O-])(=O)C.[Na+].[OH-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO.O>[CH3:26][C:27]1[N:32]=[C:31]([CH2:33][CH2:34][N:5]2[CH2:6][CH2:7][CH:8]([NH:11][S:12]([C:15]3[CH:16]=[CH:17][C:18]([NH:21][CH3:23])=[CH:19][CH:20]=3)(=[O:13])=[O:14])[CH2:9][CH2:10]2)[CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 707352-Ethenyl-6-methylpyridineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 67690431N-(4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide acetate

Product 1

HCID 22918936N-{1-[2-(6-Methyl-2-pyridyl)ethyl]-4-piperidyl}-4-(N-methylamino)benzenesulfonamideYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The N-(4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide acetate (3.71 g, 10.0 mmol), 6-methyl-2-vinylpyridine (1.43 g, 12.0 mmol) and sodium acetate (0.82 g) were dissolved in a mixture comprising methanol (20 ml) and water (20 ml). The obtained solution was heated under reflux for 5 hours, followed by the addition of sodium hydroxide (3.20 g). The obtained mixture was heated under reflux for additional three hours and acidified with 2N aqueous hydrochloric acid. The pH of the mixture was adjusted to about 8 with an aqueous solution of sodium hydrogencarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate and concentrated. The obtained oily residue was purified by column chromatography (chloroform:methanol:aqueous ammonia=90:9:1) and recrystallized from ethyl acetate/ether to give the title compound as a white crystal (2.71 g, overall yield of two steps: 70%). m.p. (°C.): 80 to 84

Workup

  1. temperatureThe obtained solution was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe obtained mixture was heated
  4. temperatureunder reflux for additional three hours
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe obtained oily residue was purified by column chromatography (chloroform:methanol:aqueous ammonia=90:9:1)
  10. customrecrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-a31a93ab971f4668b2de0a3fbc47d964
Source dataset
uspto-grants-1997_09
Patent number
US05663414

Linked notes

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