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O-Xylene → 1-Benzyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine

HRID 851134
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 851134
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2(O)[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11]2)[CH:7]=[CH:8][CH:9]=1.C1(C)C(C)=CC=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(N(CC)CC)C>O.C(OCC)(=O)C>[CH2:16]([N:12]1[CH2:13][CH2:14][CH:15]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=2)[CH2:11]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7237O-XyleneHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 136950943-(3-Methoxyphenyl)-1-benzyl-piperidine-3-ol hydrochloride

Produkt 1

HCID 151054501-Benzyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridineAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 3.25 g of the product of Step A and 65 ml of xylene was heated to 140° C. with stirring and after the addition of 2 g of phosphoric acid anhydride, the mixture was stirred at 140° C. for 2 hours and was then iced. Ice was then added to the mixture with caution and was diluted with water and ethyl acetate. The mixture was made alkaline by addition of triethylamine and was stirred until total dissolution occurred. The mixture was filtered and the decanted aqueous phase was extracted with ethyl acetate. The organic extract was washed with aqueous saturated sodium chloride solution, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 9-1 cyclohexane-ethyl acetate mixture to obtain 1.97 g of 1-benzyl-3-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine.

Aufarbeitung

  1. stirringthe mixture was stirred at 140° C. for 2 hours
  2. additionIce was then added to the mixture with caution
  3. stirringwas stirred until total dissolution
  4. filtrationThe mixture was filtered
  5. extractionthe decanted aqueous phase was extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with aqueous saturated sodium chloride solution
  8. customdried
  9. customevaporated to dryness under reduced pressure
  10. customThe residue was chromatographed over silica gel
  11. washwas eluted with a 9-1 cyclohexane-ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-b96df321c70041cc925d100de1204379
Quelldatensatz
uspto-grants-1983_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04382942

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