Potassium Carbonate → N-(4-[3-Phenylpropyl]piperidinocarbonyl)-2-phenylethenesulfonamide

HRID 1576751

Reaction equation

HRID 1576751 reaction equation
[C:1]1([CH:7]=[CH:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]1([CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][N:31]([C:34](Cl)=[O:35])[CH2:30][CH2:29]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na]>C(Cl)(Cl)Cl>[C:19]1([CH2:25][CH2:26][CH2:27][CH:28]2[CH2:29][CH2:30][N:31]([C:34]([NH:12][S:9]([CH:8]=[CH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:10])=[O:11])=[O:35])[CH2:32][CH2:33]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2575012-PhenylethenesulfonamideHCID 5360545SodiumHCID 227508054-(3-Phenylpropyl)piperidine-1-carbonyl chloride

Product 1

HCID 54287481N-(4-[3-Phenylpropyl]piperidinocarbonyl)-2-phenylethenesulfonamideYield 41%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred mixture of 1.83 g. (0.01 mole) of 2-phenylethenesulfonamide, 3.45 g. (0.025 mole) of potassium carbonate and 4.0 g. (0.015 mole) of 4-(3-phenylpropyl)piperidinocarbonyl chloride, in 75 ml. of chloroform is heated under reflux for 22 hours. The solvent is then removed by evaporation in vacuo, and to the residue is added 75 ml of 0.5N sodium hydroxide and 35 ml. of ether. The mixture is stirred for 1 hour, and then the solid which remains undissolved is removed by filtration. This affords 1.84 g. (ca. 41% yield) of the title compound as a mixture of its sodium and potassium salts.

Workup

  1. additionA stirred mixture of 1.83 g
  2. temperatureunder reflux for 22 hours
  3. customThe solvent is then removed by evaporation in vacuo
  4. additionto the residue is added 75 ml of 0.5N sodium hydroxide and 35 ml
  5. customthe solid which remains undissolved is removed by filtration

Sources & evidence

ORD record
ord-35038ab921c24664b3525e39c8a1c831
Source dataset
uspto-grants-1976_09
Patent number
US03983107

Linked notes

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