Piperazine → 1-(5-Iodopyridin-2-yl)piperazine

HRID 859913Notes

Reaction equation

HRID 859913 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CC(N(C)C)=O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 177501621-(5-Iodopyridin-2-yl)piperazineYield 82%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 2-chloro-5-iodo-pyridine (CAS number 69045-79-0, 10.52 g, 43.9 mmol) and diisopropylethylamine (11.5 mL, 65.9 mmol) in DMA (200 mL) was added piperazine (15.14 g, 0.176 mol). The mixture was then heated to 120° C. for 20 hours. The solid precipitate was then filtered off, and the filtrate evaporated in vacuo. The residue was partitioned between EtOAc (100 mL) and water (100 mL) and the layers were separated. The aqueous layer was then extracted with EtOAc (2×100 mL). The combined organic extracts were then dried, (MgSO4), filtered and concentrated in vacuo, to give 1-(5-iodopyridin-2-yl)piperazine as a yellow solid (10.42 g, 36 mmol, 82%).

Workup

  1. filtrationThe solid precipitate was then filtered off
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was partitioned between EtOAc (100 mL) and water (100 mL)
  4. customthe layers were separated
  5. extractionThe aqueous layer was then extracted with EtOAc (2×100 mL)
  6. dry with materialThe combined organic extracts were then dried, (MgSO4),
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2411752329804331ba75b8bc8614667c
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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