Trifluoroacetic acid → HCID 68734897, compound

HRID 2382193Notes

Reaction equation

HRID 2382193 reaction equation
O[C:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[CH:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1.C(O)(C(F)(F)F)=O.CCCCC>C(Cl)Cl>[C:26]1([C:2]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=2)=[C:3]2[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8003PentaneHCID 68731553HCID 68731553, compound

Product 1

HCID 68734897HCID 68734897, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(hydroxy(phenyl)(4-(trifluoromethyl)phenyl)methyl)piperidine-1-carboxylate (1.0 g, 2.29 mmol) in dry DCM (10 mL) at 0° C. was added TFA (10 mL) dropwise and the resulting solution was stirred at rt for 16 h. The solvents were removed under vacuum. The residue was diluted with DCM, washed with sodium bicarbonate solution and water, dried over sodium sulfate and concentrated under vacuum to afford crude compound which was crashed out of pentane to give 4-(phenyl(4-(trifluoromethyl)phenyl)-methylene)piperidine (0.5 g, 69%) as a grey solid. MS (ESI, pos. ion) m/z: 318 (M+1).

Workup

  1. customThe solvents were removed under vacuum
  2. additionThe residue was diluted with DCM
  3. washwashed with sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto afford crude compound which

Sources & evidence

ORD record
ord-0aa8e8178ad04e21bc50b43719d27ada
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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