Piperidine → 1,2,3,6-Tetrahydro-4-(3-methoxyphenyl)-1-methylpyridine

HRID 1156996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1156996
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](O)([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)[CH2:18][CH2:17]1.N1CCCC[CH2:31]1.[OH-].[NH4+]>CS(O)(=O)=O>[CH3:15][N:16]1[CH2:21][CH:20]=[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:31])[CH:23]=2)[CH2:18][CH2:17]1

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 14812Phosphorus oxide (P4O10)HCID 14923Ammonium HydroxideHCID 205344404-(3-Hydroxyphenyl)-1-methyl-4-piperidinol

Produkt 1

HCID 1557781,2,3,6-Tetrahydro-4-(3-methoxyphenyl)-1-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6395Methanesulfonic AcidLösungsmittel

Versuchsvorschrift

To a stirred solution of 200 ml. of 50 g. of phosphorous pentoxide in methanesulfonic acid was added portionwise over four minutes 59 g. of 1-methyl-4-hydroxy-4-(3-hydroxyphenyl)piperidine. The reaction was exothermic and the temperature rose to 70° C. After complete addition of the piperidine derivative, the reaction mixture was added to 200 g. of ice, and the aqueous mixture was made alkaline by the addition of ammonium hydroxide. The alkaline mixture was extracted several times with diethyl ether, and the ethereal extracts were combined, washed with water, dried, and the solvent was removed by evaporation under reduced pressure to provide 44.7 g. of the product as an oil. The oil thus formed was distilled to provide 1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine, B.P. 123°-138° C. at 0.1 torr.

Aufarbeitung

  1. customrose to 70° C
  2. additionthe reaction mixture was added to 200 g
  3. extractionThe alkaline mixture was extracted several times with diethyl ether
  4. washwashed with water
  5. customdried
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customto provide 44.7 g
  8. customThe oil thus formed
  9. distillationwas distilled

Quellen und Nachweise

ORD-Eintrag
ord-6972dab723cc49499acce59436a7ba4d
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04337341

Notizen zur Reaktion

Wird geladen…