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

HRID 898722

Reaction equation

HRID 898722 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-2ceda9972d994b22a1657fce47af09a7
Source dataset
uspto-grants-2008_04
Patent number
US07351828B2

Linked notes

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