Trifluoroacetic acid → (4-Ethoxy-3-fluoro-phenyl)-piperidin-4-yl-methanone

HRID 713462Notes

Reaction equation

HRID 713462 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[C:17]([F:24])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:25])=[CH:16][C:17]=1[F:24])[CH3:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 712267821,1-Dimethylethyl 4-(4-ethoxy-3-fluorobenzoyl)-1-piperidinecarboxylate

Product 1

HCID 71227114(4-Ethoxy-3-fluoro-phenyl)-piperidin-4-yl-methanoneYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-ethoxy-3-fluoro-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester (0.95 g, 2.70 mmol) in 10 mL of DCM, was added 2 mL of TFA. The reaction mixture was stirred at ambient temperature for 2.5 hours, and then solvent was removed by reduced pressure to yield the title product (0.65 g, 2.46 mmol). MS (ESI) m/z 252.0 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.43 min.

Workup

  1. customsolvent was removed by reduced pressure

Sources & evidence

ORD record
ord-caa12dae0443429795c392c7c3f4543d
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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