(3-(Piperidin-1-ylsulfonyl)phenyl)methanol → 3-(1-piperidinylsulfonyl)Benzaldehyde

HRID 1919857노트

반응식

HRID 1919857 반응식
[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(#N)C>[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[CH:16]=[O:17])(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

4

반응물 2

HCID 65750537(3-(Piperidin-1-ylsulfonyl)phenyl)methanolHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 212321303-(1-piperidinylsulfonyl)Benzaldehyde수율 81.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A solution of (3-(piperidin-1-ylsulfonyl)phenyl)methanol (160 mg, 0.627 mmol) in acetonitrile (5 mL) was added dropwise over 3 minutes to a stirred, ice-cold solution of pyridinium chlorochromate (203 mg, 0.944 mmol) in acetonitrile (5 mL). On completion of the addition the mixture was allowed to attain room temperature, and then heated to reflux for 1 hour. After cooling to ambient temperature and concentrating in vacuo, the residue was then taken up with a mixture of ethyl acetate and saturated sodium bicarbonate solution. The biphasic mixture was transferred to a separating funnel and further partitioned using brine solution. The separated organic phase was passed through a short pad of silica gel, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford 3-(piperidin-1-ylsulfonyl)benzaldehyde (130 mg, 0.51 mmol, 81%) which was used directly without further purification.

후처리

  1. additionOn completion of the addition the mixture
  2. customto attain room temperature
  3. temperatureheated
  4. temperatureto reflux for 1 hour
  5. concentrationconcentrating in vacuo
  6. additionthe residue was then taken up with a mixture of ethyl acetate and saturated sodium bicarbonate solution
  7. customThe biphasic mixture was transferred to a separating funnel
  8. customfurther partitioned
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-9398480cc8b648ff917559d03e33c046
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168673B2

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