1-Phenylpiperidine → 2-Chloro-5-(4-piperidin-1-yl-benzoyl)-benzenesulfonamide

HRID 1515455Notes

Reaction equation

HRID 1515455 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[Cl-].C([Al+]CC)C.[C:21]1([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[C:24]2[CH:23]=[CH:22][C:21]([N:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)=[CH:26][CH:25]=2)=[CH:4][C:3]=1[S:11]([NH2:12])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 200381-PhenylpiperidineHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 16686102Diethyl aluminum chloride

Product 1

HCID 581074562-Chloro-5-(4-piperidin-1-yl-benzoyl)-benzenesulfonamideYield 40.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 300 mg of 4-chloro-3-sulfamoyl-benzoyl chloride (1.186 mmol, 1 equivalent) in 20 mL of dichloromethane is stirred at room temperature as 2.37 mL of diethyl aluminum chloride (1.0 M in hexane) is added drop-wise. The reaction is stirred at room temperature for 10 minutes, then 229 mg of 1-phenyl piperidine is added. The reaction is stirred at room temperature for 30 minutes. The reaction mixture is poured onto ice-2 N HCl and extracted with dichloromethane. The aqueous layer is then basified with 2 N sodium hydroxide and extracted with dichloromethane. The combined organic extracts are washed with water, dried over sodium sulfate, and concentrated in vacuo. After purification by flash chromatography, 180 mg of product is obtained. 1H NMR (400 MHz, CDCl3): δ 1.69 (s, 6H), 3.18 (m, 1H), 3.42 (s, 3H), 5.18 (s, 2H), 6.86 (d, 2H, J=8 Hz), 7.62 (d, 1H, J=8 Hz), 7.70 (d, 2H, J=8 Hz), 7.87 (d, 1H, J=8 Hz), 8.42 (s, 1H). MS (m/z): 379 (M+1). Analytics calculated for C18H19ClN2O3S: C, 57.06; H, 5.05; N, 7.39. Found: C, 56.88; H, 5.04; N, 7.13.

Workup

  1. additionis added drop-wise
  2. stirringThe reaction is stirred at room temperature for 30 minutes
  3. additionThe reaction mixture is poured onto ice-2 N HCl
  4. extractionextracted with dichloromethane
  5. extractionextracted with dichloromethane
  6. washThe combined organic extracts are washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-459be7c187754554aeae84914c95d5b9
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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