1H-Imidazole-4-sulfonamide, 5-chloro-1-methyl-N-(3-(4-morpholinyl)propyl)-, monohydrochloride → 1H-Imidazole-4-sulfonamide, 1-methyl-N-(3-(4-morpholinyl)propyl)-

HRID 1708161

Reaction equation

HRID 1708161 reaction equation
Cl.Cl[C:3]1[N:7]([CH3:8])[CH:6]=[N:5][C:4]=1[S:9]([NH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)(=[O:11])=[O:10]>[Pd].O>[O:19]1[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][NH:12][S:9]([C:4]2[N:5]=[CH:6][N:7]([CH3:8])[CH:3]=2)(=[O:11])=[O:10])[CH2:21][CH2:20]1

Participants

4

Reactant 1

HCID 30714611H-Imidazole-4-sulfonamide, 5-chloro-1-methyl-N-(3-(4-morpholinyl)propyl)-, monohydrochloride

Product 1

HCID 30714701H-Imidazole-4-sulfonamide, 1-methyl-N-(3-(4-morpholinyl)propyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

16.7 g (46.5 mmol) of 5-chloro-N-(3-morpholino-1-propyl)-1-methyl-4-imidazolesulfonamide hydrochloride from Example 32 are hydrogenated at 25° C. and 3.45 bar in the presence of 3 g of Pd/C catalyst in 250 ml of water. The residue remaining after filtration and evaporation in vacuo is converted into the free base using saturated potassium carbonate solution, extracted with dichloromethane and recrystallized from dioxane/diisopropyl ether in order to give the crystalline title compound, identical with that as in Example 7.

Workup

  1. customare hydrogenated at 25° C.
  2. filtrationafter filtration and evaporation in vacuo
  3. extractionextracted with dichloromethane
  4. customrecrystallized from dioxane/diisopropyl ether in order

Sources & evidence

ORD record
ord-2dbbd33826244a74a46908a270ad0a05
Source dataset
uspto-grants-1994_10
Patent number
US05356922

Linked notes

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