Trifluoroacetic acid → 1-Amino-6-(4-fluorophenyl)piperidin-2-one

HRID 1803216Notes

Reaction equation

HRID 1803216 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[N:9]2[NH:15]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O>[NH2:15][N:9]1[CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][C:10]1=[O:14]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66859411Tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamate

Product 1

HCID 581101281-Amino-6-(4-fluorophenyl)piperidin-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step AAG (3): To a soln of tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamate (330 mg, 1.07 mmol) in CH2Cl2 (5 mL) was added TFA (1.00 mL, 13.0 mmol). The mixture was stirred at for 2 hrs. The solvent was removed in vacuo. The crude reaction was diluted with EtOAc (100 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 solution, dried over Na2SO4, filtered, and concentrated in vacuo to afford 1-amino-6-(4-fluorophenyl)piperidin-2-one (200 mg, 90% yield). LC-MS (M+H)+ 209.26.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude reaction
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f701bac0489543e08125eb6b6730117d
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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