1-Methylpiperazine → 4-Methyl-piperazin 1-o-tolyl-nicotinamide

HRID 1017484Notes

Reaction equation

HRID 1017484 reaction equation
C([NH:8][C:9](=[O:24])[C:10]1[C:15](C2C=CC=CC=2C)=[CH:14][C:13](Cl)=[N:12][CH:11]=1)C1C=CC=CC=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(OCC)(=O)C>[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[C:30]1([CH3:31])[CH:9]=[CH:10][CH:15]=[CH:14][C:13]=1[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:9]([NH2:8])=[O:24])[CH2:11]1

Participants

4

Reactant 2

HCID 531671-Methylpiperazine3×HCID 12167314N-benzyl-6-chloro-4-o-tolyl-nicotinamide

Product 1

HCID 1317236364-Methyl-piperazin 1-o-tolyl-nicotinamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.5 g (7.4 mMol) N-benzyl-6-chloro-4-o-tolyl-nicotinamide and 3.3 ml (29.7 mMol) N-methyl-piperazine in 25 ml ethyl acetate was heated to 80° C. for 18 hours. After adding 1.65 ml (14.8 mMol) N-methyl-piperazine, the reaction mixture was further heated 2 hours at 80° C., and after a new addition of 1.65 ml (14.8 mMol) N-methyl-piperazine 6 hours at 85° C. It was then concentrated under reduced pressure and the residue was filtered on silica gel (eluent: CH2Cl2/MeOH 5:1) to yield 2.21 g (74%) N-benzyl-6-(4-methyl-piperazin-1-o-tolyl-nicotinamide as a yellow resin.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. filtrationthe residue was filtered on silica gel (eluent: CH2Cl2/MeOH 5:1)

Sources & evidence

ORD record
ord-ee5661c9841d4100976d05f2fc325870
Source dataset
uspto-grants-2002_11
Patent number
US06479483B2

Reaction notes

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