Potassium Iodide → Methanesulfonamide, N-(4-((1-(3-(4-pyridinyl)propyl)-4-piperidinyl)carbonyl)phenyl)-, dihydrochloride

HRID 1646199Notes

Reaction equation

HRID 1646199 reaction equation
[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].C(=O)([O-])O.[Na+].Cl.[Cl:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1.[I-].[K+]>CN(C)C=O>[ClH:27].[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:28][CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[CH2:15][CH2:14]2)=[O:12])=[CH:19][CH:20]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 205441Pyridine, 4-(3-chloropropyl)-, hydrochlorideHCID 516892Sodium BicarbonateHCID 14130042N-[4-(piperidine-4-carbonyl)-phenyl]methanesulfonamide hydrochloride

Product 1

HCID 3087188Methanesulfonamide, N-(4-((1-(3-(4-pyridinyl)propyl)-4-piperidinyl)carbonyl)phenyl)-, dihydrochlorideYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

0.295 g (0.926 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride and 0.380 g (4.52 mmol) of sodium hydrogencarbonate were suspended in 4 ml of dimethylformamide and the suspension was stirred at 85° C. for 40 min. 0.20 g (1.04 mmol) of 4-(3-chloropropyl)pyridine hydrochloride and 0.31 g (1.87 mmol) of potassium iodide were added to the suspension and the mixture was stirred at 85° C. for 1.5 h. The liquid reaction mixture was filtered and the filtrate was concentrated. The obtained residue was purified according to silica gel column chromatography (chloroform:methanol:aqueous ammonia=96:4:0.4). The purified product was converted into its hydrochloride with ethanolic hydrogen chloride and recrystallized from ethanol to obtain 0.288 g (66%) of the intended compound.

Workup

  1. stirringthe mixture was stirred at 85° C. for 1.5 h
  2. customThe liquid reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customThe obtained residue was purified
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7d959498a5de4711bd705fe327f2fccf
Source dataset
uspto-grants-1993_01
Patent number
US05179095

Reaction notes

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