Piperazine → Methyl 6-piperazinonicotinate

HRID 612414Notes

Reaction equation

HRID 612414 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-piperazinonicotinateYield 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-7e8ef99418404cd982081be30a9583c0
Source dataset
uspto-grants-1999_12
Patent number
US06004961

Reaction notes

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