4-Benzylpiperazine-1-carboxamidine hemisulfate → HCID 178520340, compound

HRID 1032697Notes

Reaction equation

HRID 1032697 reaction equation
[Na].[OH:2][CH:3]=[C:4]1[CH2:9][CH2:8][O:7][C:5]1=O.S(O)(O)(=O)=O.[C:15]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)(=[NH:17])[NH2:16]>C(O)C>[CH2:24]([N:21]1[CH2:20][CH2:19][N:18]([C:15]2[N:17]=[C:3]([OH:2])[C:4]([CH2:9][CH2:8][OH:7])=[CH:5][N:16]=2)[CH2:23][CH2:22]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfateHCID 66988753HCID 66988753, compound

Product 1

HCID 178520340HCID 178520340, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.0 g (73.5 mmoles) of 2-hydroxymethylenebutyrolactone sodium salt [synthesized by the method described in J. O. Fissekis et al., J. Org., Chem. 29, 2670 (1964)] and 19.6 g (73.3 mmoles) of 1-amidino-4-benzylpiperazine sulfate were added to 360 ml of ethanol, and the solution was refluxed for 5 hours. Ethanol was evaporated, and the residue was mixed with water and extracted with chloroform. The chloroform layer was dried, concentrated, and purified by silica gel column chromatography to give 6.66 g (yield 29%) of 2-(4-benzylpiperazino)-4-hydroxy-5-(2-hydroxyethyl)pyrimidine as crystals.

Workup

  1. temperaturethe solution was refluxed for 5 hours
  2. customEthanol was evaporated
  3. additionthe residue was mixed with water
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform layer was dried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd64aadefc88404db465c46502ead374
Source dataset
uspto-grants-1990_09
Patent number
US04959368

Reaction notes

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