4-(4-Methoxyphenyl)-1-piperazinecarboximidamide → HCID 19032445, compound

HRID 266063Notes

Reaction equation

HRID 266063 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15](=[NH:17])[NH2:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl([O-])(=O)(=O)=O.[CH3:23][NH2+:24][CH3:25].C[O-].[Na+]>C(O)CC.CO>[CH3:23][N:24]([CH:10]=[N:9][C:6]1[CH:5]=[N:17][C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:14][CH2:13]2)=[N:16][CH:7]=1)[CH3:25]

Participants

6

Reactant 3

HCID 47411894-(4-Methoxyphenyl)-1-piperazinecarboximidamideHCID 10942334Sodium Methoxide2×HCID 14786861HCID 14786861, compound

Product 1

HCID 19032445HCID 19032445, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 10311-PropanolSolvent

Procedure

To a mixture of 20 g of 4-(4-methoxyphenyl)-1-piperazinecarboximidamide and 21 g of N-[3-(dimethylamino)methylene]amino]-2-propenylidene]-N-methylmethanaminium perchlorate in 200 ml of 1-propanol were added dropwise 70 ml of a solution of sodium methoxide in methanol (1M). After stirring for 2 hours there were added dropwise again 70 ml of a solution of sodium methoxide in methanol (1M). Then the mixture was stirred and refluxed for 2 hours. After cooling, the reaction mixture was evaporated and the residue was purified by column chromatography (eluent: CH2Cl2 /CH3OH 97:3). The eluent of the desired fraction was evaporated, yielding 15 g (62.5%) of N-[(dimethylamino)methylene]-2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinamine (interm. 24);

Workup

  1. stirringThen the mixture was stirred
  2. temperaturerefluxed for 2 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated
  5. customthe residue was purified by column chromatography (eluent: CH2Cl2 /CH3OH 97:3)
  6. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-4d52551ec1ff4d99afe9ddaf2fd11934
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Reaction notes

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