Potassium Carbonate → 4-Benzyl-1-[2-(3-nitrobenzenesulfonyl)ethyl]piperidine

HRID 914996Notes

Reaction equation

HRID 914996 reaction equation
CS(O[CH2:6][CH2:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)(=[O:10])=[O:9])(=O)=O.[CH2:20]([CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:20]([CH:27]1[CH2:32][CH2:31][N:30]([CH2:6][CH2:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)(=[O:10])=[O:9])[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 589580692-(3-Nitro-benzenesulfonyl)ethyl methanesulfonate

Product 1

HCID 589580954-Benzyl-1-[2-(3-nitrobenzenesulfonyl)ethyl]piperidineYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 102 (1.0 g, 3.2 mmol), 4-benzylpiperidine (103) (0.62 g, 3.5 mmol), and potassium carbonate (1.1 g, 8.0 mmol) in acetonitrile (10 ml) was heated at 70° C. overnight. It was allowed to cool to room temperature and partitioned between EtOAc (150 mL) and water (150 mL). The organic layer was washed with water (100 ml), brine (100 ml), dried over MgSO4, and concentrated. The residue was chromatographed on silica gel (8:1 to 4:1 to 2:1 hexanes/EtOAc) to give 104 (0.26 g, 21%).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc (150 mL) and water (150 mL)
  3. washThe organic layer was washed with water (100 ml), brine (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (8:1 to 4:1 to 2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-fe2f3574e2734c1f980f4c895d8bb1a7
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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