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

HRID 1913166ノート

反応式

HRID 1913166 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-94fe87ac8a374eff8e232be74e66f90f
出典データセット
uspto-grants-2013_12
特許番号
US08609696B2

反応ノート

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