2,3-Dichloropyridine → HCID 62587713, compound

HRID 1868075Notes

Reaction equation

HRID 1868075 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH:4]([CH3:8])[NH:3]1.Cl[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:16][C:15]1[C:10]([N:6]2[CH2:5][CH:4]([CH3:8])[NH:3][CH:2]([CH3:1])[CH2:7]2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 169882,3-DichloropyridineHCID 660562,6-DimethylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 62587713HCID 62587713, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-dimethylpiperazine (291 mg, 2.55 mmol) and 2,3-dichloropyridine (377.4 mg, 2.55 mmol) were charged to a microwave vial, dissolved in DMF (0.25 mL) and added with diisopropylethylamine (1.11 mL, 6.38 mmol). The reaction mixture was irradiated at 165° C. for 30 minutes. The reaction was complete as determined by TLC. After solvent removal the crud product was purified via flush column chromatography to afford 1-(3-chloropyridin-2-yl)-3,5-dimethylpiperazine in 64.4% yield (370 mg).

Workup

  1. customThe reaction mixture was irradiated at 165° C. for 30 minutes
  2. customAfter solvent removal the crud product
  3. customwas purified
  4. customvia flush column chromatography

Sources & evidence

ORD record
ord-87345c6ef5be4e568c973dda8c114930
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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