Ammonia → 1-(3-Fluorophenyl)-3,4-dihydroisoquinoline

HRID 2383032

Reaktionsgleichung

Reaktionsgleichung von HRID 2383032
P(=O)(O)(O)O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[F:20][C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=1)[C:24]([NH:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=O.N>O>[F:20][C:21]1[CH:22]=[C:23]([C:24]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][N:26]=2)[CH:35]=[CH:36][CH:37]=1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 1004Phosphoric AcidHCID 14812Phosphorus oxide (P4O10)HCID 7627373-fluoro-N-(2-phenylethyl)benzamide

Produkt 1

HCID 149989031-(3-Fluorophenyl)-3,4-dihydroisoquinolineAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Phosphoric acid (11.9 mL) was added to diphosphorus pentoxide (20.0 g) over 5 minutes. The mixture was stirred at 150° C. for 0.5 hours. 3-fluoro-N-(2-phenylethyl)benzamide (5.00 g) was added to the mixture, followed by stirring at 160° C. for 2.5 hours. After cooling, water was added to the reaction solution to which 28% aqueous ammonia was then added to be alkaline. The reaction solution was extracted with EtOAc, washed with saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 1-(3-fluorophenyl)-3,4-dihydroisoquinoline (4.87 g).

Aufarbeitung

  1. stirringby stirring at 160° C. for 2.5 hours
  2. temperatureAfter cooling
  3. additionwas then added
  4. extractionThe reaction solution was extracted with EtOAc
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e322bbcebb1e4c079f7ceffd64ce5c5e
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263607B2

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