Potassium Carbonate → HCID 58934064, compound

HRID 854393Notes

Reaction equation

HRID 854393 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH2:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[N:3]=1.[CH2:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[CH2:21]([N:28]1[CH2:33][CH2:32][N:31]([C:2]2[N:3]=[C:4]([CH2:11][S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[CH2:30][CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 58934065HCID 58934065, compound

Product 1

HCID 58934064HCID 58934064, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred mixture of 2-chloro-5-nitro-6-[(phenylsulfonyl)methyl]pyridine (1.41 g, 4.50 mmol), 1-benzylpiperazine (0.873 g, 4.95 mmol), and K2CO3 (0.683 g, 4.95 mmol) in ethanol is heated at reflux temperature for 1.5 h, cooled, diluted with water and extracted with CH2Cl2. The extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, EtOAc as eluent) to afford the title compound as an orange-yellow solid, 1.96 g (96% yield), mp 175-176° C., identified by NMR and mass spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 1.5 h
  3. temperaturecooled
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is chromatographed (silica gel, EtOAc as eluent)

Sources & evidence

ORD record
ord-f7f24a1cebba4c598ccf687f33a1b226
Source dataset
uspto-grants-2007_08
Patent number
US07259165B2

Reaction notes

Loading…