Sodium Iodide → 1-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(1,3,5-trimethyl-1H-pyrazole-4-yl)piperazine

HRID 1850498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850498
Cl[CH2:2][CH2:3][N:4]([CH2:19][CH2:20]Cl)[C:5]1[C:6]([CH3:18])=[C:7]([CH3:17])[C:8]2[O:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]=2[C:15]=1[CH3:16].[CH3:22][N:23]1[C:27]([CH3:28])=[C:26]([NH2:29])[C:25]([CH3:30])=[N:24]1.C(=O)([O-])O.[Na+].[I-].[Na+]>C(OCC)(=O)C.CN1CCCC1=O>[CH3:13][C:11]1([CH3:14])[CH2:10][C:9]2[C:15]([CH3:16])=[C:5]([N:4]3[CH2:19][CH2:20][N:29]([C:26]4[C:25]([CH3:30])=[N:24][N:23]([CH3:22])[C:27]=4[CH3:28])[CH2:2][CH2:3]3)[C:6]([CH3:18])=[C:7]([CH3:17])[C:8]=2[O:12]1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 1616031,3,5-trimethyl-1H-pyrazol-4-amineHCID 516892Sodium BicarbonateHCID 66760837N,N-bis(2-chloroethyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine

Produkt 1

HCID 594850091-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(1,3,5-trimethyl-1H-pyrazole-4-yl)piperazineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 1-methyl-2-pyrrolidone (5.0 mL) solution of N,N-bis(2-chloroethyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine (660 mg, 2.0 mmol) synthesized in Reference example 146, 1,3,5-trimethyl-1H-pyrazole-4-amine (300 mg, 2.4 mmol), sodium hydrogen carbonate (400 mg, 4.8 mmol) and sodium iodide (300 mg, 2.0 mmol) were added, and stirred at 120° C. for 16 hours. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1). The resulting solids were recrystallized from ethanol-water to obtain the title compound 320 mg (yield 42%). Melting point was 162 to 164° C. (ethanol-water).

Aufarbeitung

  1. additionwere added
  2. washwashed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1)
  6. customThe resulting solids were recrystallized from ethanol-water

Quellen und Nachweise

ORD-Eintrag
ord-8cf4ffe50cfa492fb2b6897936f74fa3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957069B2

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