Chloroform → HCID 13851719, compound

HRID 1087154Notes

Reaction equation

HRID 1087154 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:32])=[C:5]([C:21]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].C(Cl)(Cl)Cl>C(#N)C>[CH3:1][C:2]1[NH:3][C:4]([CH3:32])=[C:5]([C:21]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][N:29]([CH2:4][C:5]#[C:6][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:28][CH2:27]2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 14988365HCID 14988365, compound

Product 1

HCID 13851719HCID 13851719, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.2 Grams of methyl 2-piperazinylethyl 2,6-dimethyl- 4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 4.5 g of 3-phenylpropargyl bromide in 100 ml of acetonitrile were stirred at 30° C. for 5 hours under heating condition. After the reaction was finished, chloroform was added to the reaction mixture, and the mixture was washed with a saturated sodium hydrogen carbonate aqueous solution and water in this order, and dried with anhydrous sodium sulfate. The dried chloroform extract was concentrated by removing the solvent by evaporation, the residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane-methanol:dichloromethane=1:100). The product thus purified was then converted into a hydrochloride by adding hydrochloric acid-dioxane, and recrystallized from ethyl acetate-methanol-water to yield 1.2 g of methyl 2-[4-(3-phenyl-2-propynyl)-1-piperazinyl]ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate in the form of light yellow needle-like crystals. Melting point: 217°-220° C.

Workup

  1. temperatureunder heating condition
  2. washthe mixture was washed with a saturated sodium hydrogen carbonate aqueous solution and water in this order
  3. dry with materialdried with anhydrous sodium sulfate
  4. extractionThe dried chloroform extract
  5. concentrationwas concentrated
  6. customby removing the solvent
  7. customby evaporation
  8. customthe residue thus obtained
  9. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane-methanol:dichloromethane=1:100)
  10. customThe product thus purified
  11. additionby adding hydrochloric acid-dioxane
  12. customrecrystallized from ethyl acetate-methanol-water

Sources & evidence

ORD record
ord-e8b796d61f574d0e91b012745f0907d2
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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