Piperazine → 1-(3-Fluoro-2-pyridinyl)piperazine

HRID 1061576Notes

Reaction equation

HRID 1061576 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>C(O)CCC>[F:8][C:7]1[C:2]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 27827912-Chloro-3-fluoropyridine

Product 1

HCID 1349871-(3-Fluoro-2-pyridinyl)piperazineYield 73%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
23 °C

Procedure

The product of Example 28A (3.3 g, 0.025 mol) in n-butanol (150 mL) at 23° C. was treated with piperazine (21.5 g, 0.25 mol) and then reflux for 3 days. The reaction mixture was allowed to cool to 23° C. and concentrated under reduced pressure. The residue was slurried with water and ethyl acetate. The ethyl acetate solution was separarted, dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure to afford 3.3 g (73% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ 2.80 (m, 4H), 3.38 (m, 4H), 6.84 (m, 1H), 7.47 (m, 1H), 7.98 (m, 1H); MS (ESI) m/e 182 (M+H)+.

Workup

  1. temperaturereflux for 3 days
  2. concentrationconcentrated under reduced pressure
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-4019cb29ea4941eabe33a20579df0c32
Source dataset
uspto-grants-2005_11
Patent number
US06960589B2

Reaction notes

Loading…