Triethylamine → 2-(Methoxycarbonyl)-5-nitrophenyl 4-methylpiperazine-1-carboxylate

HRID 230066

Reaktionsgleichung

Reaktionsgleichung von HRID 230066
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[OH:13].ClC(Cl)(O[C:19](=[O:25])OC(Cl)(Cl)Cl)Cl.C(N(C(C)C)CC)(C)C.CCN(CC)CC.[CH3:43][N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>C1COCC1.C(Cl)Cl>[CH3:43][N:44]1[CH2:49][CH2:48][N:47]([C:19]([O:13][C:5]2[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=2[C:3]([O:2][CH3:1])=[O:14])=[O:25])[CH2:46][CH2:45]1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 139539Salicylic acid, 4-nitro-, methyl ester

Produkt 1

HCID 576329252-(Methoxycarbonyl)-5-nitrophenyl 4-methylpiperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a dry flask are added 2-hydroxy-4-nitro-benzoic acid methyl ester (40 mmol) (from Example 1h) and triphosgene (26.6 mmol) and DCM (100 mL). The reaction mixture is cooled to 0° C. and diisopropylethylamine (40 mmol) is added slowly. After addition the mixture is warmed to rt. After 1 h at this temperature it is refluxed for 1 h. The mixture is cooled down and the solvents are removed. THF (100 mL), Et3N (80 mmol), and N-methyl piperazine (80 mmol) are added and the mixture is stirred at rt overnight. The solvent is removed and the residue dissolved in EtOAc. Phases are separated upon addition of a 10% solution of NaHCO3. The organic phase is washed with brine, dried on Na2SO4 and evaporated. The crude is used in the following reaction.

Aufarbeitung

  1. additionAfter addition the mixture
  2. temperatureis warmed to rt
  3. temperatureAfter 1 h at this temperature it is refluxed for 1 h
  4. temperatureThe mixture is cooled down
  5. customthe solvents are removed
  6. customThe solvent is removed
  7. dissolutionthe residue dissolved in EtOAc
  8. customPhases are separated upon addition of a 10% solution of NaHCO3
  9. washThe organic phase is washed with brine
  10. customdried on Na2SO4
  11. customevaporated
  12. customThe crude is used in the following reaction

Quellen und Nachweise

ORD-Eintrag
ord-ff89afc63ad34974acc5de0ac8fb91c3
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563894B2

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