1,4-Dichlorobenzene → 4-(2,4-dichlorobenzoyl)-N-acetylpiperidine

HRID 72850

반응식

HRID 72850 반응식
[Cl-:1].[Al+3].[Cl-].[Cl-].[CH:5]1[C:10](Cl)=[CH:9][CH:8]=[C:7]([Cl:12])[CH:6]=1.[C:13]([N:16]1[CH2:24][CH2:23][CH:19]([C:20](Cl)=[O:21])[CH2:18][CH2:17]1)(=[O:15])[CH3:14]>O>[Cl:1][C:9]1[CH:8]=[C:7]([Cl:12])[CH:6]=[CH:5][C:10]=1[C:20]([CH:19]1[CH2:18][CH2:17][N:16]([C:13](=[O:15])[CH3:14])[CH2:24][CH2:23]1)=[O:21]

참가 물질

5

반응물 3

HCID 46851,4-DichlorobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 130763874-(2,4-dichlorobenzoyl)-N-acetylpiperidine수율 50%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Aluminium chloride (11, 24 g, 84 mmol) is added portionwise to 23 mL of dichlorobenzene (200 mmol). To this suspension 8 g of 1-acetylisonipecotoyl chloride (42 mmol) was added also portionwise. The mixture was stirred 10 minutes at room temperature and then at 90° C. for 4 hours until TLC indicated completion of the reaction that changed from a yellow/orange solution changed into dark orange upon heating. Water was added and the solution was extracted three times with dichloromethane. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash-chromatography on silica gel with hexane:ethyl acetate (1:0 to 0:1) to give 6.3 g (50%) of the product as an orange oil. MS (m/e): 300.2 (M+).

후처리

  1. waitat 90° C. for 4 hours until TLC indicated
  2. customcompletion of the reaction
  3. temperatureupon heating
  4. extractionthe solution was extracted three times with dichloromethane
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash-chromatography on silica gel with hexane:ethyl acetate (1:0 to 0:1)

출처 및 근거

ORD 기록
ord-d08775b157c249249f66914995cf0109
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829029B2

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