Piperazine → Methyl 6-piperazinonicotinate

HRID 1816331Notes

Reaction equation

HRID 1816331 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>CS(C)=O.O>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 14987928Methyl 6-piperazinonicotinateYield 76.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of methyl 6-chloronicotinate (25.4 g) and piperazine (38.3 g) in dimethylsulfoxide (125 ml) was heated at 100° C. for 2 hours then cooled and diluted with water, followed by extraction with ethyl acetate (4×). The combined organic layers were washed with water then dried over magnesium sulfate, filtered and evaporated to give a crude product that was triturated with isopropyl ether-hexane to yield methyl 6-(1-piperazinyl)nicotinate (25 g) as a light yellow powder.

Workup

  1. temperaturethen cooled
  2. extractionfollowed by extraction with ethyl acetate (4×)
  3. washThe combined organic layers were washed with water
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude product that
  8. customwas triturated with isopropyl ether-hexane

Sources & evidence

ORD record
ord-60650bed2290498581d4cc3209aaeade
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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