Potassium Carbonate → Methanesulfonamide, N-(4-((1-(4-pyridinylmethyl)-4-piperidinyl)carbonyl)phenyl)-, dihydrochloride

HRID 982357Notes

Reaction equation

HRID 982357 reaction equation
C[O-].[Na+].[ClH:4].[CH3:5][S:6]([NH:9][C:10]1[CH:23]=[CH:22][C:13]([C:14]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][CH:11]=1)(=[O:8])=[O:7].Cl.[Cl:25][CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[ClH:25].[ClH:4].[CH3:5][S:6]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:22][CH:23]=1)(=[O:7])=[O:8]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 10942334Sodium MethoxideHCID 14130042N-[4-(piperidine-4-carbonyl)-phenyl]methanesulfonamide hydrochloride

Product 1

HCID 3087186Methanesulfonamide, N-(4-((1-(4-pyridinylmethyl)-4-piperidinyl)carbonyl)phenyl)-, dihydrochlorideYield 33.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.13 g (18.8 mmol) of sodium methoxide was added to a suspension of 3.0 g (9.4 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride and 1.55 g (9.4 mmol) of 4-chloromethylpyridine hydrochloride in 90 ml of acetonitrile. The mixture was stirred at room temperature for 10 min. 2.88 g of potassium carbonate was added to the mixture and the obtained mixture was refluxed for 3 h. After cooling, the liquid reaction mixture was filtered and the filtrate was concentrated, while the residue was purified according to silica gel chromatography (chloroform:methanol=95:5). The product was converted into its hydrochloride with ethanolic hydrogen chloride and recrystallized from methanol/isopropanol to obtain 1.4 g of the intended compound:

Workup

  1. temperaturethe obtained mixture was refluxed for 3 h
  2. temperatureAfter cooling
  3. customthe liquid reaction mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated, while the residue
  6. customwas purified
  7. customrecrystallized from methanol/isopropanol

Sources & evidence

ORD record
ord-1fe633eea38b40aeb9800dd71fc49582
Source dataset
uspto-grants-1991_02
Patent number
US04996215

Reaction notes

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