Piperidine → HCID 69049848, compound

HRID 1984764Notes

Reaction equation

HRID 1984764 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[C:5]#[N:6].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(OC(=O)C)C>CS(C)=O>[N:14]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[C:10]([F:13])([F:12])[F:11])[C:5]#[N:6])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 27375503-Fluoro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 69049848HCID 69049848, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 3-fluoro-4-(trifluoromethyl)benzonitrile (300 mg, 1.59 mmol) in DMSO (5.0 mL) was added piperidine (675 mg, 7.93 mmol), and the mixture was stirred for 43 hours at 55° C. After the mixture was cooled to room temperature, ethylacetate was added and washed with water then brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane:ethylacetate=10:1) to afford 3-piperidin-1-yl-4-(trifluoromethyl)benzonitrile (353 mg, 88% yield).

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethylacetate=10:1)

Sources & evidence

ORD record
ord-9e5b61ad08ed40deb13661dd3026b38d
Source dataset
uspto-grants-2009_06
Patent number
US07544716B2

Reaction notes

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