Benzenesulfonyl chloride, 3,4-dichloro- → HCID 22220483, compound

HRID 1061353Notes

Reaction equation

HRID 1061353 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[Cl:25][C:26]1[CH:27]=[C:28]([S:33](Cl)(=[O:35])=[O:34])[CH:29]=[CH:30][C:31]=1[Cl:32]>C(Cl)Cl>[Cl:25][C:26]1[CH:27]=[C:28]([S:33]([NH:2][C:3]2[CH:8]=[CH:7][C:6]([N:9]3[CH2:10][CH2:11][C:12](=[O:15])[CH2:13][CH2:14]3)=[CH:5][CH:4]=2)(=[O:34])=[O:35])[CH:29]=[CH:30][C:31]=1[Cl:32]

Participants

5

Reactant 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 81531DiisopropylethylamineHCID 222202401-(4-Amino-phenyl)-piperidin-4-one hydrochloride

Product 1

HCID 22220483HCID 22220483, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.5 g (1.9 mmol) of the hydrochloride salt of 1-(4-amino-phenyl)-piperidine-4-one (which was obtained in Example 224) in 10 mL of anhydrous methylene chloride was added 0.99 mL (5.7 mmol) of diisopropylethyl amine. After 10 minutes of stirring, 0.51 g (2.1 mmol) of 3,4-dichlorobenzene sulfonyl chloride was added and the mixture was allowed to stir overnight. The reaction mixture was quenched with water and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed twice with water, twice with brine, dried over sodium sulfate and then concentrated in vacuo. The residue was then purified by flash chromatography (10% EtOAc in hexanes to 50% EtOAc in hexanes) and the title compound was collected as 0.25 g of a yellow solid; 1H NMR (300 MHz, CDCl3) δ 2.55 (t, J=6.09 Hz, 4H), 3.58 (t, J=6.03 Hz, 4H), 6.33 (s, 1H), 6.60-6.88 (m, 2H), 6.95-7.00 (m, 2H), 7.50 (d, J=1.47 Hz, 2H), 7.78-7.79 (m, 1H); MS (ES) m/z: 398.8 (MH+); HRMS found for C17H16Cl2N2O3S: 398.0227.

Workup

  1. stirringto stir overnight
  2. customThe reaction mixture was quenched with water
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed twice with water, twice with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by flash chromatography (10% EtOAc in hexanes to 50% EtOAc in hexanes)
  9. customthe title compound was collected as 0.25 g of a yellow solid

Sources & evidence

ORD record
ord-9d2a05e3d9f44fd08574e35fe5f7a7e2
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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