Acetic Acid → N-(4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide acetate

HRID 1377022Notes

Reaction equation

HRID 1377022 reaction equation
[C:1]([N:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH3:5])(=[O:3])[CH3:2].[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18]1.[C:30]([OH:33])(=[O:32])[CH3:31].[H][H]>C(O)C.[Pd]>[CH2:23]([N:20]1[CH2:21][CH2:22][CH:17]([NH:16][S:12]([C:9]2[CH:10]=[CH:11][C:6]([N:4]([C:1](=[O:3])[CH3:2])[CH3:5])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[CH2:18][CH2:19]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1.[C:30]([OH:33])(=[O:32])[CH3:31].[NH:20]1[CH2:21][CH2:22][CH:17]([NH:16][S:12]([C:9]2[CH:10]=[CH:11][C:6]([N:4]([C:1](=[O:3])[CH3:2])[CH3:5])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[CH2:18][CH2:19]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 2931464-(N-methylacetamido)benzene-1-sulfonyl chlorideHCID 4158521-Benzyl-4-piperidylamineHCID 178418361HCID 178418361, compound

Product 2

HCID 15049722N-(1-Benzyl-4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamideHCID 67690431N-(4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide acetateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(1-Benzyl-4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide was prepared as a colorless oil from the 4-(N-acetyl-N-methylamino)benzenesulfonyl chloride (20.0 g, 80.8 mmol) and 4-amino-1-benzylpiperidine (18.16 ml, 88.9 mmol) in a similar manner to that described in Preparative Example 16. This oil was dissolved in ethanol (200 ml), followed by the addition of glacial acetic acid (10.0 ml). The obtained mixture was stirred in the presence of 10% palladium/carbon (water-containing one, 2.00 g) in a hydrogen atmosphere (1 atm) at 50° C. for 5 hours and filtered to remove the catalyst. The filtrate was concentrated to precipitate a crystal. The resulting mixture was washed with ethyl acetate and filtered to give the title compound as a white crystal (29.70 g, overall yield of two steps: 100%). m.p.: 177 to 184

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated
  4. customto precipitate a crystal
  5. washThe resulting mixture was washed with ethyl acetate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-4d29072cf90c4196afe111f57606e9a8
Source dataset
uspto-grants-1997_09
Patent number
US05663414

Reaction notes

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