1-Methylpiperazine → 3-Pyridinecarboxamide, N-methyl-6-(4-methyl-1-piperazinyl)-

HRID 379369Notes

Reaction equation

HRID 379369 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>>[CH3:9][NH:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([N:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 531671-Methylpiperazine2×HCID 123642306-Chloro-N-methylnicotinamide

Product 1

HCID 30429373-Pyridinecarboxamide, N-methyl-6-(4-methyl-1-piperazinyl)-Yield 1,011.7%

Conditions

Temperature
100 °C

Procedure

A mixture of 52.0 g (30.5 mmol) 6-chloro-N-methyl-nicotinamide and 176 ml (1.58 mol) 1-methylpiperazine was heated at 100° C. for 1.5 h in an autoclave. After cooling to room temperature excess 1-methylpiperazine was removed by distillation. The residue was partitioned in 1000 ml dichloromethane/1 N aqueous sodium hydroxide solution. The layers were separated and the aqueous layer was extracted with three 500 ml portions of dichloromethane. Concentration and short column chromatography yielded 72.3 g (97%) of the title compound as a light brown solid.

Workup

  1. customwas removed by distillation
  2. customThe residue was partitioned in 1000 ml dichloromethane/1 N aqueous sodium hydroxide solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with three 500 ml portions of dichloromethane
  5. concentrationConcentration and short column chromatography

Sources & evidence

ORD record
ord-6810dfee7f7142a2820c706e17a20f72
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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