Hydrochloric Acid → HCID 20074046, compound

HRID 704444Notes

Reaction equation

HRID 704444 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[NH:15][CH:14]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:20][CH2:19]3)=[O:17])[CH2:13][S:12]2)[CH:6]=[N:7][C:8]=1[O:9]C.Cl>C(OCC)(=O)C.O1CCOCC1>[CH3:1][O:2][CH:3]1[C:8](=[O:9])[N:7]=[CH:6][C:5]([CH:11]2[NH:15][CH:14]([C:16]([N:18]3[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:22][CH2:23]3)=[O:17])[CH2:13][S:12]2)=[CH:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14881563HCID 14881563, compound

Product 1

HCID 20074046HCID 20074046, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1-[2-(5,6-Dimethoxy-3-pyridyl)thiazolidin-4-ylcarbonyl]-4-(3-phenylpropyl)piperazine (730 mg) was dissolved in 25 ml of ethyl acetate. To the solution was added with stirring at room temperature 2N hydrogen chloride solution in dioxane. The resultant powder was collected by filtration and dissolved in saturated sodium carbonate solution. Ethyl acetate was added, the organic layer was separated and washed with water, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 25 ml; 10% methanol-ethyl acetate) to give 210 mg of 1-[2-(5-methoxy-6 oxo 5,6-dihydro-3-pyridyl)thiazolidin-4-ylcarbonyl]-4-(3-phenylpropyl)piperazine.

Workup

  1. additionTo the solution was added
  2. filtrationThe resultant powder was collected by filtration
  3. dissolutiondissolved in saturated sodium carbonate solution
  4. additionEthyl acetate was added
  5. customthe organic layer was separated
  6. washwashed with water
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (silica gel 25 ml; 10% methanol-ethyl acetate)

Sources & evidence

ORD record
ord-0e48d80a79d2402485676bd68e71082c
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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