Naphthalene → 2-Naphthyl 4-piperidyl ketone hydrochloride

HRID 1389860

Reaktionsgleichung

Reaktionsgleichung von HRID 1389860
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH:12]1[CH2:20][CH2:19][CH:15]([C:16]([Cl:18])=[O:17])[CH2:14][CH2:13]1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>ClCC(Cl)(Cl)Cl>[ClH:18].[NH:12]1[CH2:20][CH2:19][CH:15]([C:16]([C:7]2[CH:8]=[CH:9][C:10]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[CH:6]=2)=[O:17])[CH2:14][CH2:13]1

Komponenten

6

Edukt 4

HCID 931NaphthaleneHCID 14798Sodium HydroxideHCID 3016318Piperidine-4-carbonyl chloride hydrochlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 202955472-Naphthyl 4-piperidyl ketone hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 124181,1,1,2-TetrachloroethaneLösungsmittel

Versuchsvorschrift

To a slurry of 99 g of naphthalene (0.75 mole) and 96 g of isonipecotic acid chloride hydrochloride (0.5 mole) in tetrachloroethane is added over a period of 10 minutes 200 g (1.5 moles) of aluminum chloride. The reaction mixture is allowed to stand at room temperature for 10 minutes, then decomposed by pouring it over ice water, made basic with a 50% NaOH solution, and extracted with diethyl ether. The ether layer is dried over magnesium sulfate, filtered, and treated with ethereal HCl. The resulting oil is dissolved in warmed methanol, treated with charcoal, filtered and diluted with butanone. The methanol is removed by distillation, adding more butanone as needed. The solution is cooled overnight, and the resulting solid filtered off and recrystallized from methanol-butanone to give the desired product. M.P. 251°-253° C.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. dry with materialThe ether layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. additiontreated with ethereal HCl
  5. dissolutionThe resulting oil is dissolved in warmed methanol
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. additiondiluted with butanone
  9. customThe methanol is removed by distillation
  10. additionadding more butanone
  11. temperatureThe solution is cooled overnight
  12. filtrationthe resulting solid filtered off
  13. customrecrystallized from methanol-butanone

Quellen und Nachweise

ORD-Eintrag
ord-c1bd6f6359024cd89eee81529156c6a4
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04246268

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