Trifluoroacetic acid → 1-(2-(2-Fluoropyridin-3-YL)piperidin-1-YL)ethanone

HRID 410284Notes

Reaction equation

HRID 410284 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[C:14]([O:16]C(C)(C)C)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:21](O)(C(F)(F)F)=O.C(OC(=O)C)(=O)C>C(Cl)Cl>[F:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[C:14](=[O:16])[CH3:21])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 59327149Tert-butyl 2-(2-fluoropyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 593269601-(2-(2-Fluoropyridin-3-YL)piperidin-1-YL)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2-fluoropyridin-3-yl)piperidine-1-carboxylate (70 mg, 0.250 mmol) and DCM (5 mL) was added TFA (0.50 mL, 6.49 mmol). After 1 hour, the reaction was washed with 10% Na2CO3. The organic layer was treated with TEA (0.070 mL, 0.499 mmol), then acetic anhydride (0.024 mL, 0.250 mmol). After 15 minutes, LC-MS shows conversion to the desired product [M+1=223]. The reaction was washed with water and concentrated in vacuo to give 1-(2-(2-fluoropyridin-3-yl)piperidin-1-yl)ethanone as a yellow oil.

Workup

  1. washthe reaction was washed with 10% Na2CO3
  2. waitAfter 15 minutes

Sources & evidence

ORD record
ord-37835a7bbfb94b878231530e7bb6f6e7
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

Loading…