4-Benzylpiperazine-1-carboxamidine hemisulfate → HCID 178471120, compound

HRID 1032695Notes

Reaction equation

HRID 1032695 reaction equation
[CH:1]([CH:3]([CH:9]([CH3:13])[C:10]([O-:12])=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=O.S(O)(O)(=O)=O.[C:19]([N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)(=[NH:21])[NH2:20].C(O[K])(C)(C)C>>[CH2:28]([N:25]1[CH2:24][CH2:23][N:22]([C:19]2[N:21]=[C:10]([OH:12])[C:9]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:1])=[CH:13][N:20]=2)[CH2:27][CH2:26]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfateHCID 22164846Ethyl 2-formyl-3-methylsuccinateHCID 178418922HCID 178418922, compound

Product 1

HCID 178471120HCID 178471120, compoundYield 23%

Procedure

A solution of 2.16 g (10 mmoles) of ethyl 2-formyl-3-methylsuccinate [Zhur. Obshche i Khim., 30, 2250 (1960)] was added to a mixture of 2.67 g (10 mmoles) of 1-amidino-4-benzylpiperazine sulfate, 1.12 g (10 mmoles) of tert-C4H9OK and 12 ml of tert-C4O9OH. The mixture was then refluxed for 6 hours. The reaction mixture was cooled, and extracted by adding water and CHCl3. The CHCl3 layer was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2 :CH3OH=95:5) to give 0.68 g (yield 23%) of 2-(4-benzylpiperazino)-5-(1-ethoxycarbonylethyl)-4-hydroxypyrimidine.

Workup

  1. temperatureThe mixture was then refluxed for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted
  4. additionby adding water and CHCl3
  5. dry with materialThe CHCl3 layer was dried over anhydrous MgSO4
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (CH2Cl2 :CH3OH=95:5)

Sources & evidence

ORD record
ord-4b85eb89b24b45459510d1a69a365f00
Source dataset
uspto-grants-1990_09
Patent number
US04959368

Reaction notes

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