1-Methylpiperazine → N-methyl-6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinamide

HRID 379412Notes

Reaction equation

HRID 379412 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>[OH-].[Na+]>[CH3:9][NH:8][C:6](=[O:7])[C:5]1[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:11][C:2]([N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 121673126-chloro-N-methyl-4-o-tolyl-nicotinamide

Product 1

HCID 15481065N-methyl-6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinamideYield 83.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3.2 g (12.2 mmol) 6-chloro-N-methyl-4-o-tolyl-nicotinamide in 6.7 ml (60.3 mmol) 1-methylpiperazine was stirred at 100° C. for 2.5 h. The reaction mixture was cooled to r.t., treated with 10 ml 0.1N NaOH and extracted. The aqueous phase was separated and extracted twice with THF and the organic phases were washed twice with brine. The combined organic phases were dried over Na2SO4, the solvent was removed under reduced pressure and the residue purified by chromatography over silica gel (CH2Cl2: MeOH=99:1) to yield 3.3 g (83.7%) product as beige foam.

Workup

  1. extractionextracted
  2. customThe aqueous phase was separated
  3. extractionextracted twice with THF
  4. washthe organic phases were washed twice with brine
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customthe residue purified by chromatography over silica gel (CH2Cl2: MeOH=99:1)

Sources & evidence

ORD record
ord-eefe8b99b07941b6a93ec93469bdf05b
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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