1,4-Difluorobenzene → 1-Acetyl-4-(2,5-difluorobenzoyl)piperidine

HRID 3966

반응식

HRID 3966 반응식
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](Cl)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1>>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:11])[C:22]2[CH:23]=[C:18]([F:17])[CH:19]=[CH:20][C:21]=2[F:24])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

4

반응물 3

HCID 108921,4-DifluorobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 138001311-Acetyl-4-(2,5-difluorobenzoyl)piperidine수율 52.1%

실험 절차

To a stirred suspension of 100 g of 1-acetyl-4-piperidine carboxylic acid chloride in 500 ml of 1,4-difluorobenzene was added in aliquots, 211 g of anhydrous aluminum chloride. The mixture was stirred at reflux under nitrogen for 3 hrs and allowed to cool to room temperature. The mixture was poured into ice and extracted twice with ethyl acetate. The extracts were washed with saturated sodium bicarbonate solution and dried over anhydrous potassium carbonate. Filtration followed by evaporation of the solvent provided an oil which crystallized on standing. The solid was washed with cyclohexane and dried to provide 73.3 g (52.1%) of 1-acetyl-4-(2,5-difluorobenzoyl)piperidine: mp 82°-87° C. Recrystallization from a mixture of isopropyl alcohol, diisopropyl ether and hexane provided product with mp 93°-95° C.

후처리

  1. temperatureat reflux under nitrogen for 3 hrs
  2. additionThe mixture was poured into ice
  3. extractionextracted twice with ethyl acetate
  4. washThe extracts were washed with saturated sodium bicarbonate solution
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationFiltration
  7. customfollowed by evaporation of the solvent
  8. customprovided an oil which
  9. customcrystallized
  10. washThe solid was washed with cyclohexane
  11. customdried

출처 및 근거

ORD 기록
ord-8b653410a1d44cdf9990edd4a831a13b
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723009

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