Bromine → 1-(5-Bromopyrimidin-2-yl)piperazine

HRID 364621Notes

Reaction equation

HRID 364621 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[Br:13]Br>Cl>[Br:13][C:5]1[CH:6]=[N:1][C:2]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 887471-(2-Pyrimidinyl)piperazine

Product 1

HCID 27571751-(5-Bromopyrimidin-2-yl)piperazineYield 62%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

This example serves to illustrate procedure B of Scheme 2. To an ice-cooled solution of 1-(2-pyrimidinyl)piperazine (16.4 g, 0.1 mole) in 1N HCl (100 mL) was added dropwise bromine (15.98 g, 0.1 mole). After stirring at 0° for 0.5 hr, the mixture was heated to 100° until dissipation of the red color had occurred. The mixture is filtered, cooled, made alkaline with 50% NaOH and extracted with ether. The dried extract (MgSO4) was concentrated in vacuo to provide 14.5 g (62%) of product, m.p. 73°-75°.

Workup

  1. temperaturethe mixture was heated to 100° until dissipation of the red color
  2. filtrationThe mixture is filtered
  3. temperaturecooled
  4. extractionextracted with ether
  5. extractionThe dried extract (MgSO4)
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-c3ca85b0010e449b8758d7dfd7ba1914
Source dataset
uspto-grants-1986_08
Patent number
US04605655

Reaction notes

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