Methanol → Sodium 6-(4-ethylpiperazinyl)pyridine-3-carboxylate

HRID 1003316Notes

Reaction equation

HRID 1003316 reaction equation
[OH-].[Na+:2].CO.[CH2:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)[CH3:6]>O>[CH2:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[N:18]=[CH:17][C:16]([C:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH2:11][CH2:12]1)[CH3:6].[Na+:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 14987929Methyl 6-(4-ethylpiperazin-1-yl)nicotinate

Product 1

HCID 23663821Sodium 6-(4-ethylpiperazinyl)pyridine-3-carboxylateYield 111.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.1 g of sodium hydroxide in 15 ml of water was added to 75 ml of methanol. 15 g of methyl 6-(4-ethyl-1-piperazinyl)pyridine-3-carboxylate was added and the mixture was heated under reflux for 1.5 hours. The solvent was distilled off under reduced pressure, to the resulting residue was added hot acetone and the crystal thus precipitated out was recovered by filtration. It was again washed with hot acetone to afford 17.2 g of the title compound as a crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. distillationThe solvent was distilled off under reduced pressure, to the resulting residue
  4. additionwas added hot acetone
  5. customthe crystal thus precipitated out
  6. filtrationwas recovered by filtration
  7. washIt was again washed with hot acetone

Sources & evidence

ORD record
ord-9f1225e7359d460ea87081127b400aa0
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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