Hydrochloric Acid → 6-Chloro-2-naphthyl 4-piperidyl ketone

HRID 1389861

Reaktionsgleichung

Reaktionsgleichung von HRID 1389861
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19](Cl)=[O:20])[CH2:15][CH2:14]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=3)[CH:8]=2)=[O:20])[CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 70562-ChloronaphthaleneHCID 3016318Piperidine-4-carbonyl chloride hydrochlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 543200266-Chloro-2-naphthyl 4-piperidyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 3.15 g (19.4 mmoles) of 2-chloronaphthalene and 4.46 g (24.2 mmoles) of 4-piperidinecarbonyl chloride hydrochloride in 60 ml nitrobenzene is added gradually 9.7 g (73 mmoles) of aluminum chloride. The mixture is heated to 65°-70° C. for 2 hours and cooled. Ice water and concentrated HCl are added to the reaction mixture. The solid precipitate is partitioned between aqueous sodium hydroxide solution and ether and the organic phase washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue is recrystallized from cyclohexane to yield 6-chloro-2-naphthyl 4-piperidyl ketone. M.P. 98°-100°-5°.

Aufarbeitung

  1. temperatureThe mixture is heated to 65°-70° C. for 2 hours
  2. temperaturecooled
  3. customThe solid precipitate is partitioned between aqueous sodium hydroxide solution and ether
  4. washthe organic phase washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is recrystallized from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-dbb77250e2ca4d9e96ef11d4b596969e
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04246268

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