Water → 4-amino-5-chloro-2-methoxy-N-((1-(4-phenylsulfonylbutyl)piperidin-4-yl)methyl)benzamide hydrochloride

HRID 344472Notes

Reaction equation

HRID 344472 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([S:13]([CH2:16][CH2:17][CH2:18][CH2:19][Cl:20])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.Cl.[NH2:23][C:24]1[C:39]([Cl:40])=[CH:38][C:27]([C:28]([NH:30][CH2:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[O:29])=[C:26]([O:41][CH3:42])[CH:25]=1.O>CN(C)C=O>[ClH:20].[NH2:23][C:24]1[C:39]([Cl:40])=[CH:38][C:27]([C:28]([NH:30][CH2:31][CH:32]2[CH2:33][CH2:34][N:35]([CH2:19][CH2:18][CH2:17][CH2:16][S:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)(=[O:14])=[O:15])[CH2:36][CH2:37]2)=[O:29])=[C:26]([O:41][CH3:42])[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12457347((4-Chlorobutyl)sulfonyl)benzeneHCID 699663304-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride

Product 1

HCID 700729264-amino-5-chloro-2-methoxy-N-((1-(4-phenylsulfonylbutyl)piperidin-4-yl)methyl)benzamide hydrochlorideYield 13.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.87 g) and 4-phenylsulfonylbutyl chloride (0.40 g) were added to a solution (15 ml) of 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (0.52 g) in dimethylformamide, and the mixture was stirred at 70°-80° C. for 7.5 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The obtained oil was treated with hydrochloric acid-ethanol and the obtained crystals were recrystallized from ethyl acetate to give 0.10 g of 4-amino-5-chloro-2-methoxy-N-((1-(4-phenylsulfonylbutyl)piperidin-4-yl)methyl)benzamide hydrochloride.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography
  6. additionThe obtained oil was treated with hydrochloric acid-ethanol
  7. customthe obtained crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3d1d3eb1a05d48099cd4559b3de05707
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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