Water → HCID 86678769, compound

HRID 1620597Notes

Reaction equation

HRID 1620597 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[C:17]([F:20])([F:19])[F:18])[CH2:5][CH2:4]1.C(N(CC)CC)C.O>CS(C)=O>[CH:2]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[C:17]([F:20])([F:18])[F:19])[CH2:5][CH2:4]1)=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 71246386HCID 71246386, compound

Product 1

HCID 86678769HCID 86678769, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-[4-(hydroxymethyl)piperidin-1-yl]-3-(trifluoromethyl)benzonitrile (3.55 g) in DMSO (50 mL) were added triethylamine (10.6 mL) and sulfur trioxide pyridine complex (6.63 g). The reaction mixture was stirred at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.06 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-02d829268c634ebaa1df8b00e8148744
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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