Trifluoroacetic acid → HCID 58494028, compound

HRID 1942701Notes

Reaction equation

HRID 1942701 reaction equation
[Br:1][C:2]1[C:3]([CH2:22][CH3:23])=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>ClCCl>[Br:1][C:2]1[C:3]([CH2:22][CH3:23])=[C:4]([CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58494134HCID 58494134, compound

Product 1

HCID 58494028HCID 58494028, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[(3-bromo-2-ethylphenyl)methylidene]-1-piperidinecarboxylate (D136) (3 g, 7.89 mmol) in Dichloromethane (DCM) (100 mL) was added TFA (6.08 mL, 79 mmol). The reaction solution was stirred at room temperature for 2 hours. The solvent was evaporated in vacuo to afford 4-[(3-bromo-2-ethylphenyl)methylidene]piperidine (D137) (1.9 g), which was used directly without further purification. MS (ES): C14H18BrN requires 279.1. found 280.1 (M+H+).

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ef8232f7304a4b6296c012b04eab0639
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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