Sodium Hydroxide → 3-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]-5-amine

HRID 2211749

Reaktionsgleichung

Reaktionsgleichung von HRID 2211749
[B-](F)(F)(F)F.[N:6]#[O+].[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:21]3([CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[O:20][C:19]3[C:28]([CH3:34])=[C:29]([CH3:33])[CH:30]=[C:31]([CH3:32])[C:18]2=3)=[CH:13][CH:12]=1)([CH3:10])[CH3:9].[OH-].[Na+]>C(#N)C>[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:21]3([CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]3)[O:20][C:19]3[C:28]([CH3:34])=[C:29]([CH3:33])[C:30]([NH2:6])=[C:31]([CH3:32])[C:18]2=3)=[CH:13][CH:12]=1)([CH3:10])[CH3:9]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 11137142Nitrilooxonium tetrafluoroborateHCID 219613123-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]

Produkt 1

HCID 219613023-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]-5-amineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A solution of nitrosyl tetrafluoroborate (470.7 mg, 4.03 mmol) in acetonitrile (40 ml) was cooled to 0° C. To the solution was added a solution of 3-(4-isopropylphenyl)-1′,4,6,7-tetramethylspiro[benzofuran-2(3H),4′-piperidine] (479.1 mg, 1.32 mmol) in acetonitrile (10 ml) and the mixture was stirred for 20 minutes. The reaction mixture was poured into ice water and basified with an 8 N aqueous solution of sodium hydroxide. The product was extracted twice with ethyl acetate. The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was dissolved into ethanol (20 ml) and palladium-carbon (59.9 mg) was added into the solution, then the mixture was stirred at 60° C. for 18 hours under a hydrogen atmosphere. The reaction mixture was cooled down to room temperature, filtered to remove insoluble materials, and then concentrated under reduced pressure. The residue was subjected to column chromatography (on Chromatorex NHDM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.); hexane-ethyl acetate 3:1) to obtain 402.0 mg (83% yield) of the title compound. Melting point: 123-124° C. (Hexane).

Aufarbeitung

  1. extractionThe product was extracted twice with ethyl acetate
  2. washThe combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved into ethanol (20 ml) and palladium-carbon (59.9 mg)
  7. additionwas added into the solution
  8. stirringthe mixture was stirred at 60° C. for 18 hours under a hydrogen atmosphere
  9. filtrationfiltered
  10. customto remove insoluble materials
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-23440ce2fbd14538b210e4cd3a2d1ec7
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101867B2

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