Dimethyl Sulfoxide → 1-{[4-(Pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carbaldehyde

HRID 1913166노트

반응식

HRID 1913166 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:26]2[CH2:31][CH2:30][CH:29]([CH2:32][OH:33])[CH2:28][CH2:27]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl.O>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:18]=[CH:19][C:20]([S:23]([N:26]2[CH2:31][CH2:30][CH:29]([CH:32]=[O:33])[CH2:28][CH2:27]2)(=[O:24])=[O:25])=[CH:21][CH:22]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58494552(1-{[4-(Pyridin-2-yl)phenyl]sulfonyl}piperidin-4-yl)methanol

생성물 1

HCID 584945611-{[4-(Pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carbaldehyde수율 99.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

To a stirred solution of oxalyl chloride (92 μL, 1.07 mmol) in DCM (2 mL) at −78° C. is added dropwise a solution of dimethyl sulfoxide (0.15 mL, 2.16 mmol) in DCM (2 mL). After 15 mins a solution of (1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidin-4-yl)methanol (0.26 g, 0.79 mmol) in DCM (2 mL) is added dropwise. After another 15 mins, triethylamine (0.425 mL, 3.04 mmol) is added and the reaction is allowed to warm to room temperature. Stirring is continued for 18 h. The mixture is diluted with water and extracted with DCM. The organic layers are combined, dried over Na2SO4, filtered and concentrated under reduced pressure to give 0.26 g (99%) of 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carbaldehyde. m/z=331.

후처리

  1. waitis continued for 18 h
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-94fe87ac8a374eff8e232be74e66f90f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609696B2

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