Triethylamine → HCID 59750100, compound

HRID 748352Notes

Reaction equation

HRID 748352 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.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2([OH:43])[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][CH:32]=1.C(OCC)(=O)C>CN(C=O)C.O>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2([OH:43])[CH2:38][CH2:39][N:40]([CH2:18][C:16]3[N:17]=[C:12]([C:4]4[S:5][C:6]5[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=5[C:2](=[O:1])[N:3]=4)[CH:13]=[CH:14][CH:15]=3)[CH2:41][CH2:42]2)=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 865964626-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridylmethanesulfonate

Product 1

HCID 59750100HCID 59750100, compoundYield 50.1%

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 4-(4-chlorophenyl)-4-hydroxypiperidine (0.20 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-ethylacetate to give the titled compound (0.20 g, 49%) 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-ethylacetate

Sources & evidence

ORD record
ord-d3ffd780413f4c38a5bf568861580dfc
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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