Dimethyl Sulfoxide → 1-(Methylsulfonyl)piperidine-4-carbaldehyde

HRID 429820Notes

Reaction equation

HRID 429820 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][S:12]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13].C(N(CC)CC)C>ClCCl>[CH3:11][S:12]([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18352755(1-(Methylsulfonyl)piperidin-4-yl)methanol

Product 1

HCID 109543721-(Methylsulfonyl)piperidine-4-carbaldehydeYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethylsulfoxide (39 ml, 0.55 mole) in dichloromethane (300 ml) was added slowly to a solution of oxalyl chloride (22.7 ml, 0.264 mole) in dichloromethane (700 ml) at −60° C. After 10 minutes a solution of 1-methanesulfonylpiperidine-4-methanol (46 grams. 0.238 mole) in dichloromethane (500 ml) was added slowly. After 30 minutes at −60° C., triethylamine (167 ml) was added. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (1.2 liters) and water (200 ml). The organic phase was dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to give 1-methanesulfonylpiperidine-4-carboxaldehyde (34 grams), m.p. 97° C.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (1.2 liters) and water (200 ml)
  3. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-17a21b5be76149768f8a603b6672d50d
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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