Piperidine → HCID 86688930, compound

HRID 404668Notes

Reaction equation

HRID 404668 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>C(#N)C>[F:13][C:9]1[CH:8]=[C:7]([CH:2]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:3]([O:5][CH3:6])=[O:4])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 57495616Methyl 2-bromo-2-(3-fluorophenyl)acetate

Product 1

HCID 86688930HCID 86688930, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-bromo-2-(3-fluorophenyl)acetate (310 mg, 1.25 mmol), piperidine (0.15 ml, 1.51 mmol), and DIPEA (0.26 ml, 1.51 mmol) were dissolved in acetonitrile (15 ml) and stirred at room temperature for 16 hours. The solvent was evaporated and the crude was purified by flash chromatography (petroleum ether/EtOAc=9/1) to afford methyl 2-(3-fluorophenyl)-2-(piperidin-1-yl)acetate (224 mg, 71% yield) as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. customthe crude was purified by flash chromatography (petroleum ether/EtOAc=9/1)

Sources & evidence

ORD record
ord-2002643b8173492fa440e1c574b11f04
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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