Piperidine → HCID 59750127, compound

HRID 499531Notes

Reaction equation

HRID 499531 reaction equation
CS(O[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[S:13][C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16](=[O:18])[N:17]=2)[N:7]=1)(=O)=O.[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.N1CCCC[CH2:31]1.C(OCC)(=O)C>CN(C=O)C.O>[N:25]1([CH2:23][C:6]2[N:7]=[C:8]([C:12]3[S:13][C:14]4[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=4[C:16](=[O:18])[N:17]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:28][CH2:29][CH2:31][CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 229392726-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate

Product 1

HCID 59750127HCID 59750127, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate (0.30 g, 0.86 mmol), triethylamine (0.20 ml, 1.42 mmol) and piperidine (0.081 g, 0.95 mmol) were dissolved in DMF (30 ml), and the mixture was stirred at 70° C. for 18 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from n-hexane-ethyl acetate to give the titled compound (0.16 g, 54%) as pale yellow crystals.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-10092896a7de4b169bfa4bf6ad391958
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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