1,1'-Carbonyldiimidazole → N-(1-Methylethyl)-N'-[3-(4-methyl-1-piperazinyl)propyl]-N-[2-(phenylsulfonyl)ethyl]urea maleate

HRID 4226

Reaction equation

HRID 4226 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13].[C:24]1([S:30]([CH2:33][CH2:34][NH:35][CH:36]([CH3:38])[CH3:37])(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43]>O1CCCC1.CO>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[CH3:37][CH:36]([N:35]([CH2:34][CH2:33][S:30]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:31])=[O:32])[C:12]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]1)=[O:13])[CH3:38]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 444266Maleic AcidHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamine

Product 1

HCID 14050290N-(1-Methylethyl)-N'-[3-(4-methyl-1-piperazinyl)propyl]-N-[2-(phenylsulfonyl)ethyl]urea maleateYield 68.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 6.00 g (0.035 mole) of 1-(3-aminopropyl)-4-methylpiperazine and 6.97 g (0.043 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.17 g (0.036 mole) of N-(2-phenylsulfonylethyl)-2-propanamine in 100 ml of tetrahydrofuran was added, and the mixture was refluxed for 16 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and water. The solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. The oil was dissolved in methanol; a solution of two equivalents of maleic acid in methanol was added, and a white solid precipitated. This was collected to give 15.48 g (68.8%) of white crystalline solid; m.p. 162°-163° C. with decomposition.

Workup

  1. temperaturethe mixture was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and water
  4. dry with materialThe solution was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. customa white solid precipitated
  8. customThis was collected

Sources & evidence

ORD record
ord-54b66e4802a3406cb2dc05cb341eaba1
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Linked notes

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