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

HRID 1772744Notes

Reaction equation

HRID 1772744 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)=[N:6][CH:7]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 164142271-(5-Bromopyridin-2-yl)piperazineYield 76%

Conditions

Temperature
130 °C

Procedure

A mixture of 5-bromo-2-chloropyridine (110 g, 573 mmol) and piperazine (99.1 g, 1.15 mol) was stirred overnight at 130° C. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (200 mL) and then extracted with DCM (3×200 mL). The combined organic layers were concentrated under reduced pressure to obtain compound 90a as a white solid (105 g, 76% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C9H12BrN3: 242.0 (M+H). found 242.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (200 mL)
  3. extractionextracted with DCM (3×200 mL)
  4. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-65208fb7e04e4891acabcb684258d75e
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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