Piperidine → HCID 59750127, compound

HRID 748349Notes

Reaction equation

HRID 748349 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18]S([O-])(=O)=O)[CH:15]=[CH:14][CH:13]=2)=[N:3]1.C(N(CC)CC)C.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(OCC)(=O)C>CN(C=O)C.O>[N:30]1([CH2:18][C:16]2[N:17]=[C:12]([C:4]3[S:5][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[C:2](=[O:1])[N:3]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 865964626-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridylmethanesulfonate

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-pyridylmethanesulfonate (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-17ff836186ed4e42952f2b7fb49f2ac1
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

Loading…