Trifluoroacetic acid → 1-Phenyl-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indole

HRID 565679

Reaktionsgleichung

Reaktionsgleichung von HRID 565679
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.FC(F)(F)C(O)=O.[C:17]1([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.N>C(O)(=O)C>[C:17]1([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([C:6]3[CH2:5][CH2:4][NH:3][CH2:8][CH:7]=3)=[CH:24]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 1820291-Phenyl-1H-indoleHCID 2723901PiperonylamineHCID 12896473Azane;hydrate

Produkt 1

HCID 221111271-Phenyl-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indoleAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a heated (110° C.) mixture of 4-piperidone monohydrate hydrochloride (8.2 g), acetic acid (15 mL) and trifluoroacetic acid (30 mL) was added 1-phenyl-1H-indole (3.1 g) under nitrogen atmosphere over a period of 25 min. The mixture was stirred for 30 minutes at 120° C., then cooled and poured into ice. This was neutralized with conc. ammonia water under cooling and the product was extracted thrice with ethyl acetate. The combined extract was washed with water followed by saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was provided for the next reaction without further purification. Yield 63%. Amorphous.

Aufarbeitung

  1. temperatureTo a heated
  2. temperaturecooled
  3. additionpoured into ice
  4. temperatureunder cooling
  5. extractionthe product was extracted thrice with ethyl acetate
  6. extractionThe combined extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was provided for the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-962fd7bdf84944b1a7453bfae665d5d4
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172085B2

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