Triethylamine → 2-{6-[(4-Phenyl-1-piperidyl)methyl]-2-pyridyl}-4H-1,3-benzothiazine-4-one

HRID 499532Notes

Reaction equation

HRID 499532 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.[C:30]1([CH:36]2CCNCC2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(OCC)(=O)C>CN(C=O)C.O>[C:30]1([CH:36]2[CH2:29][CH2:28][N:25]([CH2:23][C:6]3[N:7]=[C:8]([C:12]4[S:13][C:14]5[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=5[C:16](=[O:18])[N:17]=4)[CH:9]=[CH:10][CH:11]=3)[CH2:26][CH2:27]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 698734-PhenylpiperidineHCID 229392726-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate

Product 1

HCID 597503172-{6-[(4-Phenyl-1-piperidyl)methyl]-2-pyridyl}-4H-1,3-benzothiazine-4-oneYield 76%

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 4-phenylpiperidine (0.15 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, 76%) 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-76cc64a2f373469b958eceb48446f7e3
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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