Trifluoroacetic acid → 4-(4-Chlorophenyl)piperidine

HRID 1487902Notes

Reaction equation

HRID 1487902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 27281794tert-Butyl 4-(4-chlorophenyl)piperidine-1-carboxylate2×

Product 1

HCID 12036134-(4-Chlorophenyl)piperidineYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 250-mL round-bottom flask, was placed a solution of tert-butyl 4-(4-chlorophenyl)piperidine-1-carboxylate (compound 42.3, 5.00 g, 16.9 mmol) in dichloromethane (100 mL), trifluoroacetic acid (9.6 g, 84 mmol). The resulting solution was stirred overnight at room temperature and then concentrated under reduced pressure. The residue was carefully diluted with ethyl acetate (100 mL) and aqueous sodium bicarbonate was added until a pH of 8 was attained. The resulting mixture was washed with brine (100 mL) and the organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound as a light yellow solid (2.30 g, 70%).

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was carefully diluted with ethyl acetate (100 mL) and aqueous sodium bicarbonate
  4. additionwas added until a pH of 8
  5. washThe resulting mixture was washed with brine (100 mL)
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04b77c7bab63448cb62235be6df206dc
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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