Phosphorus oxychloride → 1-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline

HRID 242085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 242085
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=4)[CH2:16][CH2:15][N:14]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 604097221-(4-Chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclobutanecarboxamide

Produkt 1

HCID 668686991-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

1-(4-Chlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]cyclobutanecarboxamide (10.58 g, 30.8 mmol) was treated with toluene (100 mL). Phosphoryl trichloride (4.72 g, 30.8 mmol) was added and the reaction mixture was heated under reflux for 8 h. After cooling to room temperature the reaction mixture was concentrated in vacuo and then slowly poured in ice water. Ethyl acetate was added and the organic layer was washed with water (2×), dried (MgSO4) and concetrated in vacuo to give an orange oil. Yield: 10.25 g.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 8 h
  3. concentrationwas concentrated in vacuo
  4. additionslowly poured in ice water
  5. additionEthyl acetate was added
  6. washthe organic layer was washed with water (2×)
  7. dry with materialdried (MgSO4)
  8. customto give an orange oil

Quellen und Nachweise

ORD-Eintrag
ord-4f76c4855d6246aca806863959e6bead
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653100B2

Notizen zur Reaktion

Wird geladen…