P-Toluenesulfonamide → N-[4-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]-1-oxobutyl]-4-methyl-benzenesulfonamide

HRID 915548Notes

Reaction equation

HRID 915548 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)[CH2:9][CH2:8]1.[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:28][CH:29]=1.CN(C1C=CC=CN=1)C.CCN=C=NCCCN(C)C>ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][C:16]([NH:33][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:23])=[CH:25][CH:26]=2)(=[O:31])=[O:32])=[O:18])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 6269P-ToluenesulfonamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 694203114-(3,4-Dichlorophenoxy)-1-piperidinebutanoic acid hydrochloride

Product 1

HCID 69418750N-[4-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]-1-oxobutyl]-4-methyl-benzenesulfonamideYield 12.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3,4-Dichlorophenoxy)-1-piperidinebutanoic acid hydrochloride (0.250 g) was dissolved in dichloromethane (10 mL) containing p-toluenesulfonamide (0.142 g), dimethylaminopyridine (92 mg) and EDCI (0.158 g) were added. The solution was stirred at room temperature for 4 days. The solvent was evaporated. The crude product was dried in vacuo and then purified by HPLC (at column dilution, gradient ammonium acetate/acetonitrile 75% to 5% ;Waters Xterra® column) and to give the title compound (42 mg).

Workup

  1. additionwere added
  2. customThe solvent was evaporated
  3. dry with materialThe crude product was dried in vacuo
  4. custompurified by HPLC (at column dilution, gradient ammonium acetate/acetonitrile 75% to 5% ;Waters Xterra® column)

Sources & evidence

ORD record
ord-78a1118f2fe149669a35b69e2a69d9a9
Source dataset
uspto-grants-2007_09
Patent number
US07265227B2

Reaction notes

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