Pentane → 3-(Phenyl(4-(trifluoromethyl)phenyl)methyl)piperidine

HRID 2382187Notes

Reaction equation

HRID 2382187 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[C:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].CCCCC>CO.[Pd]>[C:1]1([CH:7]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)[CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8003PentaneHCID 687345843-(Phenyl(4-(trifluoromethyl)phenyl)methylene)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 687345103-(Phenyl(4-(trifluoromethyl)phenyl)methyl)piperidineYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(phenyl(4-(trifluoromethyl)phenyl)methylene)piperidine (1.0 g, 3.15 mmol) in methanol (25 mL) was charged with Pd/C under nitrogen atmosphere and fitted with hydrogen balloon using stopcock and covered with Teflon. The reaction mixture was stirred under hydrogen atmosphere for 8 h. It was filtered through celite, the celite was washed with methanol, and the solvent was removed under reduced pressure to afford the crude product which was then crashed out of pentane to give pure 3-(phenyl(4-(trifluoromethyl)phenyl)-methyl)piperidine (1.0 g, 98% yield) as a grey oil. MS (ESI, pos. ion) m/z: 320 (M+1).

Workup

  1. filtrationIt was filtered through celite
  2. washthe celite was washed with methanol
  3. customthe solvent was removed under reduced pressure
  4. customto afford the crude product which

Sources & evidence

ORD record
ord-711f1e37505e41bda5207720d6ccd7d1
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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