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

HRID 72850

反応式

HRID 72850 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-d08775b157c249249f66914995cf0109
出典データセット
uspto-grants-2014_09
特許番号
US08829029B2

関連ノート

読み込み中…