Dimethyl Sulfoxide → 1-Benzoylpiperidine-4-carbaldehyde

HRID 278249Notes

Reaction equation

HRID 278249 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:19]([N:16]1[CH2:17][CH2:18][CH:13]([CH:12]=[O:11])[CH2:14][CH2:15]1)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 102628704-Piperidinemethanol, 1-benzoyl-

Product 1

HCID 156812841-Benzoylpiperidine-4-carbaldehydeYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1.99 g of dimethyl sulfoxide in 45 mL methylene chloride at −78° C. was added 2.16 g of oxalyl chloride. After 10 min, 1.865 g of 4-hydroxymethyl-N-benzoylpiperidine (Step B) in 15 mL of methylene chloride was added at −78° C. and stirred for 30 min. DIEA (5.49 mL) was added and this mixture was stirred for an additional 30 min. at −78° C. and then warmed to room temperature and stirred another 30 min. The reaction was quenched with 50 mL water and extracted with 3×50 mL methylene chloride. The combined organic layers were dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed with 2:1 hexane:ethyl acetate followed by 1:1 hexane : ethyl acetate to give 1.445 g of the title compound.

Workup

  1. stirringthis mixture was stirred for an additional 30 min. at −78° C.
  2. stirringstirred another 30 min
  3. customThe reaction was quenched with 50 mL water
  4. extractionextracted with 3×50 mL methylene chloride
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed with 2:1 hexane

Sources & evidence

ORD record
ord-8d1e9718db8a44798a00a00e787a108f
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Reaction notes

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