Benzenesulfonyl chloride → HCID 69663205, compound

HRID 2212101Notes

Reaction equation

HRID 2212101 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([S:17]([C:20]([CH3:33])([CH3:32])[CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH:26]([NH:30]C)[CH2:25]2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:34](N(CC)CC)C>ClCCl>[C:11]1([S:17]([C:20]([CH3:33])([CH3:32])[CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH:26]([NH:30][S:7]([C:1]3([CH3:34])[CH:6]=[CH:5][CH:4]=[CH:3][CH2:2]3)(=[O:9])=[O:8])[CH2:25]2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 69663521HCID 69663521, compound

Product 1

HCID 69663205HCID 69663205, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzenesulfonyl chloride (90 μL, 0.7 mmol) was added to a solution of 1-(4-benzenesulfonyl-4-methylpentyl)-3-(methylamino)piperidine (0.22 g, 0.65 mmol) and triethylamine (180 μL, 1.3 mmol) in dichloromethane (5 ml). The reaction was stirred at room temperature for 30 minutes. The mixture was diluted with dichloromethane and washed with water (×2). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 2–5% methanol/dichloromethane, to give the title compound (220 mg, 76%).

Workup

  1. washwashed with water (×2)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with 2–5% methanol/dichloromethane

Sources & evidence

ORD record
ord-2f85eae993f4462396a9237234194c49
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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