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

HRID 80914

Reaction equation

HRID 80914 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.O>C1(C)C=CC=CC=1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 164142271-(5-Bromopyridin-2-yl)piperazineYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
130 °C

Procedure

A mixture of piperazine (107 g, 1.24 mol) and 2-chloro-5-bromopyridine (30 g, 156 mmol) in toluene (150 mL) was heated at 130° C. for 2 hours, The reaction mixture was cooled to room temperature and toluene (400 mL) and water (200 mL) were added. The organic phase was isolated and the aqeuous phase was extracted once with toluene (100 mL). The collected organic phases were washed with water (150 mL) and brine (100 mL), dried over magnesium sulphate and evaporated to dryness in vacuo to give 30.1 g (80%) of 1-(5-bromopyridin-2-yl)-piperazine.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic phase was isolated
  3. extractionthe aqeuous phase was extracted once with toluene (100 mL)
  4. washThe collected organic phases were washed with water (150 mL) and brine (100 mL)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-7891133c7fb9466eab26c0967f32c960
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Linked notes

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