Trifluoroacetic acid → (3-Bromo-5-(trifluoromethyl)phenyl)(piperidin-4-yl)methanone

HRID 2200129Notes

Reaction equation

HRID 2200129 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21](=[O:33])[C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([Br:32])[CH:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.CCOC(C)=O>ClCCl>[Br:32][C:24]1[CH:23]=[C:22]([C:21]([CH:18]2[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)=[O:33])[CH:27]=[C:26]([C:28]([F:30])([F:31])[F:29])[CH:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 90029693HCID 90029693, compound

Product 1

HCID 90020499(3-Bromo-5-(trifluoromethyl)phenyl)(piperidin-4-yl)methanoneYield 135.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add trifluoroacetic acid in dichloromethane (20%, 5 mL) to the solution of tert-butyl-4-(3-bromo-5-(trifluoromethyl)benzoyl)piperidine-1-carboxylate (387 mg, 0.88 mmol) in dichloromethane (5 mL) at 0° C., stir the mixture. TLC (PE:EtOAc=5:1) shows the reaction is complete. Concentrate under reduced pressure to dryness to afford the crude product (400 mg, 100%) which is used directly in next step. MS: (M+1): 336.0.

Workup

  1. concentrationConcentrate under reduced pressure to dryness

Sources & evidence

ORD record
ord-4ed2c7f96a894190aa2ce5e345bb2ad7
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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