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

HRID 1600478Notes

Reaction equation

HRID 1600478 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][N:15]=1>C(#N)C>[I:20][C:17]1[CH:18]=[CH:19][C:14]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 177501621-(5-Iodopyridin-2-yl)piperazineYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of piperazine (215 mg, 2.5 mmol) and potassium carbonate (890 mg, 6.45 mmol) in acetonitrile (5 mL) was added 2-chloro-5-iodopyridine (300 mg, 1.25 mmol) (prepared in Example 2(a)). The mixture was heated at reflux for 26 h and allowed to cool. It was then filtered and the solvents removed under reduced pressure. Column chromatograpgy of the residue on silica gel (dichloromethane:methanol:ammonia solution 100:5:1) gave 1-(5-iodopyridin-2-yl)-piperazine as a yellow solid (215 mg, 60%). δH (300 MHz DMSO-d6) 2.76 (4H, m, piperazinyl ), 3.40 (4H, m, piperazinyl ), 6.72 (1H, d, J=9.0), 7.77 (1H, dd, J=2.4 and 9.0), 8.25 (1H, d, J=2.4), ESMS 290 (MH+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 26 h
  3. temperatureto cool
  4. filtrationIt was then filtered
  5. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-e1df4b91333d4b88825199d8c66003df
Source dataset
uspto-grants-1999_11
Patent number
US05976497

Reaction notes

Loading…