Sodium Hydroxide → 4-Phenyl-4-piperidinocyclohexanone

HRID 543462노트

반응식

HRID 543462 반응식
[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:8][CH2:9][C:10](=[O:13])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 1621714-Phenyl-4-piperidinocyclohexanol

생성물 1

HCID 133067564-Phenyl-4-piperidinocyclohexanone수율 93%

시약·촉매·용매 3

HCID 10219390chromium (VI) trioxide촉매HCID 176Acetic Acid용매2회HCID 962Water용매

실험 절차

4-Phenyl-4-piperidinocyclohexanol (1.2 g, 4.6 mmoles) was dissolved in 50 ml of glacial acetic acid. The solution was cooled with an external ice-bath. Chromium trioxide (1 g, 10 mmole) was dissolved in 10 ml of water and 15 ml of glacial acetic acid, and was slowly added to the solution. After completion, the solution was stirred at room temperature for 4 hours. TLC analysis indicated no starting material was left. The solution was cooled with an ice-bath and was carefully made basic with sodium hydroxide solution. The greenish solution was extracted with 5×60 ml of ethyl ether. The combined ethereal solutions were dried over sodium sulfate and were concentrated under reduced pressure to give a white solid residue. Recrystallization from hexane gave 1.1 g of slightly brown crystalline solid (mp: 116°-117° C.) in 93% yield.

후처리

  1. temperatureThe solution was cooled with an external ice-bath
  2. waitwas left
  3. temperatureThe solution was cooled with an ice-bath
  4. extractionThe greenish solution was extracted with 5×60 ml of ethyl ether
  5. dry with materialThe combined ethereal solutions were dried over sodium sulfate
  6. concentrationwere concentrated under reduced pressure
  7. customto give a white solid residue
  8. customRecrystallization from hexane

출처 및 근거

ORD 기록
ord-495d0cf6ea214ae9838786e35fd84560
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04446065

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