Piperazine → Methyl 6-(piperazin-1-yl)pyridine-3-carboxylate

HRID 367258Notes

Reaction equation

HRID 367258 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8](Br)=[N:9][CH:10]=1)=[O:4].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 13349623Methyl 6-bromopyridine-3-carboxylate

Product 1

HCID 14987928Methyl 6-(piperazin-1-yl)pyridine-3-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromopyridine-5-carboxylic acid methyl ester (1.40 g, 6.5 mmol) and piperazine (5.59 g, 65 mmol) was dissolved in acetonitrile (50 ml) and heated at reflux temperature for 2.5 h. The reaction mixture was concentrated in vacuo, dissolved in dichloromethane (50 ml) and extracted with water (3×50 ml). The organic solution was dried (MgSO4) and evaporated in vacuo, affording 0.80 g (56%) of 2-(1-piperazinyl)-5-pyridinecarboxylic acid methyl ester.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in dichloromethane (50 ml)
  5. extractionextracted with water (3×50 ml)
  6. dry with materialThe organic solution was dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2317f5255dca4a91bef9ffbdca3ae0cc
Source dataset
uspto-grants-2000_10
Patent number
US06133268

Reaction notes

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