Piperazine → 1-(3-Chloropyridin-2-yl)piperazine

HRID 490211Notes

Reaction equation

HRID 490211 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][N:9]=1>C(O)CCC>[Cl:14][C:13]1[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 169882,3-Dichloropyridine

Product 1

HCID 114129441-(3-Chloropyridin-2-yl)piperazineYield 72%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of piperazine (29.1 g, 338 mmol), 2,3-dichloropyridine (5.00 g, 33.8 mmol), and n-butanol (220 mL) was refluxed for 3 days. The reaction mixture was cooled to 23° C. and concentrated under reduced pressure. The residue was slurried with ethyl acetate and water. The ethyl acetate layer was poured off and dried over sodium sulfate, filtered, and concentrated to afford 4.8 g (72% yield) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.83 (m, 4H), 3.15 (m, 4H), 6.97 (dd, 1H, J=4.5, 7.5 Hz), 7.77 (dd, 1H, J=1.5, 7.5 Hz), 8.21 (dd, 1H, J=1.5, 4.5 Hz)); MS (ESI) m/e 198 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe ethyl acetate layer was poured off
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1c6ccaf02b7e438ca87d4280cd9a80aa
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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