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

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>>[F:8][C:5]1[CH:6]=[CH:7][C:2]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:3][CH:4]=1

Participants

Reactant 2

HCID 4837Piperazine

HCID 27831712-Bromo-5-fluoropyridine

Product 1

HCID 137130231-(5-Fluoropyridin-2-yl)piperazine

Procedure

With stirring, 500 mg (2.84 mmol) of 2-bromo-5-fluoropyridine and 1.22 g (14.2 mmol) of piperazine are heated at 150° C. for 24 h. After cooling, excess piperazine is distilled off in vacuo (Kugelrohr, 1.5 mbar, 120° C.). The residue is purified by flash chromatography (dichloromethane/ethanol/conc. ammonia solution, 30:1:0.1).

Workup

temperatureAfter cooling
distillationexcess piperazine is distilled off in vacuo (Kugelrohr, 1.5 mbar, 120° C.)
customThe residue is purified by flash chromatography (dichloromethane/ethanol/conc. ammonia solution, 30:1:0.1)

Sources & evidence

ORD record: ord-84e79d5888d345bdab079d1b04396663
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919489B2

Reaction notes

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