Sodium hydride → HCID 11557815, compound

HRID 1437745Notes

Reaction equation

HRID 1437745 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[H-].[Na+].[Cl:10][C:11]1[CH:16]=[C:15](Cl)[CH:14]=[C:13]([Cl:18])[N:12]=1>CS(C)=O>[Cl:10][C:11]1[CH:16]=[C:15]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:14]=[C:13]([Cl:18])[N:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27665Pyridine, 2,4,6-trichloro-HCID 531671-Methylpiperazine

Product 1

HCID 11557815HCID 11557815, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-methyl piperazine (0.604 g, 6.04 mmol) in dry DMSO (6 mL) was prepared and NaH (0.2637 g, 10.98 mmol) was added. The resulting mixture was stirred for 30 minutes at 0° C., after which time 2,4,6-trichloropyridine (1.0 g) was added. The reaction mixture was stirred at 20 to 40° C. for 4 hours. In the reaction mixture ice cold water was added and extracted with ethyl acetate giving 3-4 times water washing. The organic layer was dried and concentrated. The residue was purified by column chromatography using 100-200 mesh silica gel. Elution of the column with 20% acetone in hexanes gave the pure product as a colorless solid. Yield: 26%.

Workup

  1. customwas prepared
  2. stirringThe reaction mixture was stirred at 20 to 40° C. for 4 hours
  3. additionIn the reaction mixture ice cold water was added
  4. extractionextracted with ethyl acetate giving 3-4 times water washing
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. washElution of the column with 20% acetone in hexanes

Sources & evidence

ORD record
ord-4badc69fe51d4f93b368621f62906f0d
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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