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

HRID 1913166Notes

Reaction equation

HRID 1913166 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-94fe87ac8a374eff8e232be74e66f90f
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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