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

HRID 1389861

반응식

HRID 1389861 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-dbb77250e2ca4d9e96ef11d4b596969e
출처 데이터셋
uspto-grants-1981_01
특허 번호
US04246268

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