1-Methylpiperazine → HCID 54410292, compound

HRID 1163874Notes

Reaction equation

HRID 1163874 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[N:24]1C(=O)C(=CC2C=CC=CC=2)S[C:25]1=[S:37])(=O)C.[CH3:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>CO>[C@@H:6]1([NH:24][C:25]([N:42]2[CH2:43][CH2:44][N:39]([CH3:38])[CH2:40][CH2:41]2)=[S:37])[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 54028629HCID 54028629, compound

Product 1

HCID 54410292HCID 54410292, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-5-benzylidenerhodanine(1.102 g., 0.002 mole) was added to a solution of N-methylpiperazine(2.40 g., 0.024 mole) in 50 ml. of methanol in a pressure bottle. The reaction mixture was stirred at room temperature for 18 hours. The mixture was filtered and the filtrate was evaporated to a brownish heavy syrup below 30° in vacuo. The residual syrup was dissolved in the minimum amount of acetone, and anhydrous ether was added to the solution to give a sticky precipitate. The supernatant was decanted, and the residual solid was dissolved in the minimum amount of methanol. Anhydrous ether was added to the solution to give a yellow precipitate. The solid was filtered, partially dissolved in ethyl acetate, and then chromatographed on a column of silica gel(1×20 cm) using ethyl acetate as the first solvent(50 ml.) and methanol as the second solvent(200 ml.). The 200 ml. of methanol effluent was reduced to ca. 20 ml. and was set aside at 5° for 24 hours. The white precipitate was filtered, washed with methanol, and dried at room temperature in vacuo, yielding 0.325 g.(50.6%); m.p. 175°-177°(dec.).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to a brownish heavy syrup below 30° in vacuo
  3. dissolutionThe residual syrup was dissolved in the minimum amount of acetone, and anhydrous ether
  4. additionwas added to the solution
  5. customto give a sticky precipitate
  6. customThe supernatant was decanted
  7. dissolutionthe residual solid was dissolved in the minimum amount of methanol
  8. additionAnhydrous ether was added to the solution
  9. customto give a yellow precipitate
  10. filtrationThe solid was filtered
  11. dissolutionpartially dissolved in ethyl acetate
  12. customchromatographed on a column of silica gel(1×20 cm)
  13. waitand was set aside at 5° for 24 hours
  14. filtrationThe white precipitate was filtered
  15. washwashed with methanol
  16. customdried at room temperature in vacuo
  17. customyielding 0.325 g

Sources & evidence

ORD record
ord-e4eccaffaa584e95922ccb1769dfa70e
Source dataset
uspto-grants-1983_01
Patent number
US04367226

Reaction notes

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